Dataset for the Synthesis of N-alkoxycarbonyl pyrroles from O-substituted carbamates – A synthetically enabling pyrrole protection strategy

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2,2,2-Trichloroethyl carbamate.zip

data 17255 4 61723 document 17255 2,2,2-Trichloroethyl 1H-pyrrole-1-carboxylate (13).zip application/zip 1cd4e1864b2d7e6250faa874b21de646 MD5 67436054 2023-07-05 09:19:04 https://researchdata.bath.ac.uk/1255/3/2%2C2%2C2-Trichloroethyl%201H-pyrrole-1-carboxylate%20%2813%29.zip 1255 3 3 application/zip other en public cc_by

2,2,2-Trichloroethyl 1H-pyrrole-1-carboxylate (13).zip

data 17256 2 61727 document 17256 (9H-Fluoren-9-yl)methyl 1H-pyrrole-1-carboxylate.zip application/zip 28b17605bc4ab62fce083c06451dc195 MD5 62297287 2023-07-05 09:20:06 https://researchdata.bath.ac.uk/1255/4/%289H-Fluoren-9-yl%29methyl%201H-pyrrole-1-carboxylate.zip 1255 4 4 application/zip other en public cc_by

(9H-Fluoren-9-yl)methyl 1H-pyrrole-1-carboxylate.zip

data 17257 2 61729 document 17257 Benzyl 1H-pyrrole-1-carboxyate (9).zip application/zip a56be12cf610b4ed5e7e4dfbc4636858 MD5 3351597 2023-07-05 09:20:43 https://researchdata.bath.ac.uk/1255/5/Benzyl%201H-pyrrole-1-carboxyate%20%289%29.zip 1255 5 5 application/zip other en public cc_by

Benzyl 1H-pyrrole-1-carboxyate (9).zip

data 17258 2 61731 document 17258 (Adamantan-1-yl)(1H-pyrrol-2-yl)methanone (24).zip application/zip d52ea0f82c1621854faeed0af993f338 MD5 68849889 2023-07-05 09:20:48 https://researchdata.bath.ac.uk/1255/6/%28Adamantan-1-yl%29%281H-pyrrol-2-yl%29methanone%20%2824%29.zip 1255 6 6 application/zip other en public cc_by

(Adamantan-1-yl)(1H-pyrrol-2-yl)methanone (24).zip

data 17259 2 61733 document 17259 1-(1H-Pyrrol-2-yl)ethan-1-one (18).zip application/zip 736273c0ee84cb60d1e7a8e9f2790036 MD5 1686934 2023-07-05 09:21:18 https://researchdata.bath.ac.uk/1255/7/1-%281H-Pyrrol-2-yl%29ethan-1-one%20%2818%29.zip 1255 7 7 application/zip other en public cc_by

1-(1H-Pyrrol-2-yl)ethan-1-one (18).zip

data 17260 2 61735 document 17260 Methyl 2-acetyl-1H-pyrrole-1-carboxylate (14).zip application/zip 347db9851521b5941540e1b361f8be06 MD5 67482547 2023-07-05 09:21:52 https://researchdata.bath.ac.uk/1255/8/Methyl%202-acetyl-1H-pyrrole-1-carboxylate%20%2814%29.zip 1255 8 8 application/zip other en public cc_by

Methyl 2-acetyl-1H-pyrrole-1-carboxylate (14).zip

data 17261 2 61737 document 17261 2,2-Dimethyl-1-(1H-pyrrol-3-yl)propan-1-one (32).zip application/zip a85a331504e8b87640bf47bc5f0e06a3 MD5 63986956 2023-07-05 09:22:22 https://researchdata.bath.ac.uk/1255/9/2%2C2-Dimethyl-1-%281H-pyrrol-3-yl%29propan-1-one%20%2832%29.zip 1255 9 9 application/zip other en public cc_by

2,2-Dimethyl-1-(1H-pyrrol-3-yl)propan-1-one (32).zip

data 17262 2 61739 document 17262 2,2-Dimethyl-1-(1-tosyl-1H-pyrrol-3-yl)propan-1-one (31).zip application/zip e9ae050f01cf23a13dce9a8a604b3d3f MD5 61806811 2023-07-05 09:22:48 https://researchdata.bath.ac.uk/1255/10/2%2C2-Dimethyl-1-%281-tosyl-1H-pyrrol-3-yl%29propan-1-one%20%2831%29.zip 1255 10 10 application/zip other en public cc_by

2,2-Dimethyl-1-(1-tosyl-1H-pyrrol-3-yl)propan-1-one (31).zip

data 17263 2 61741 document 17263 Allyl 1H-pyrrole-1-carboxylate (11).zip application/zip 7d184b0ef4acb878b5bd1ba6cf2f4451 MD5 68849865 2023-07-05 09:23:18 https://researchdata.bath.ac.uk/1255/11/Allyl%201H-pyrrole-1-carboxylate%20%2811%29.zip 1255 11 11 application/zip other en public cc_by

Allyl 1H-pyrrole-1-carboxylate (11).zip

data 17264 2 61743 document 17264 2,2-Diphenyl-1-(1H-pyrrol-2-yl)ethan-1-one (26).zip application/zip 53f614d3941d4483a1b06a3c34408a1a MD5 69501513 2023-07-05 09:24:02 https://researchdata.bath.ac.uk/1255/12/2%2C2-Diphenyl-1-%281H-pyrrol-2-yl%29ethan-1-one%20%2826%29.zip 1255 12 12 application/zip other en public cc_by

2,2-Diphenyl-1-(1H-pyrrol-2-yl)ethan-1-one (26).zip

data 17265 2 61745 document 17265 2,2,2-Trichloroethyl 2-acetyl-1H-pyrrole-1-carboxylate (17).zip application/zip 2747d9c683c0dc55b5748e22eb53373a MD5 80911444 2023-07-05 09:24:36 https://researchdata.bath.ac.uk/1255/13/2%2C2%2C2-Trichloroethyl%202-acetyl-1H-pyrrole-1-carboxylate%20%2817%29.zip 1255 13 13 application/zip other en public cc_by

2,2,2-Trichloroethyl 2-acetyl-1H-pyrrole-1-carboxylate (17).zip

data 17266 2 61747 document 17266 4-Chloro-1-(1H-pyrrol-2-yl)butan-1-one (22).zip application/zip 569ab62a6d1e8d138e3628a4b0a05a78 MD5 67293918 2023-07-05 09:25:07 https://researchdata.bath.ac.uk/1255/14/4-Chloro-1-%281H-pyrrol-2-yl%29butan-1-one%20%2822%29.zip 1255 14 14 application/zip other en public cc_by

4-Chloro-1-(1H-pyrrol-2-yl)butan-1-one (22).zip

data 17267 2 61749 document 17267 1-(1H-Pyrrol-3-yl)tetradecan-1-one (20).zip application/zip 3e8fd64ef609cce3100e912512ee8a4d MD5 66544741 2023-07-05 09:25:40 https://researchdata.bath.ac.uk/1255/15/1-%281H-Pyrrol-3-yl%29tetradecan-1-one%20%2820%29.zip 1255 15 15 application/zip other en public cc_by

1-(1H-Pyrrol-3-yl)tetradecan-1-one (20).zip

data 17268 2 61751 document 17268 2,2,2-Trichloroethyl 2-(2,2-diphenylacetyl)-1H-pyrrole-1-carboxylate (25).zip application/zip 220399df910d1b27c7003c742f38566d MD5 69070887 2023-07-05 09:26:12 https://researchdata.bath.ac.uk/1255/16/2%2C2%2C2-Trichloroethyl%202-%282%2C2-diphenylacetyl%29-1H-pyrrole-1-carboxylate%20%2825%29.zip 1255 16 16 application/zip other en public cc_by

2,2,2-Trichloroethyl 2-(2,2-diphenylacetyl)-1H-pyrrole-1-carboxylate (25).zip

data 17269 2 61753 document 17269 2,2,2-Trichloroethyl 2-(adamantane-1-carbonyl)-1H-pyrrole-1-carboxylate (23).zip application/zip 0dd160fd24d585cc38c0c5e66034f196 MD5 71370392 2023-07-05 09:26:48 https://researchdata.bath.ac.uk/1255/17/2%2C2%2C2-Trichloroethyl%202-%28adamantane-1-carbonyl%29-1H-pyrrole-1-carboxylate%20%2823%29.zip 1255 17 17 application/zip other en public cc_by

2,2,2-Trichloroethyl 2-(adamantane-1-carbonyl)-1H-pyrrole-1-carboxylate (23).zip

data 17270 2 61755 document 17270 (9H-Fluoren-9-yl)methyl 2-acetyl-1H-pyrrole-1-carboxylate (16).zip application/zip ffe8b3a8d778d52ecd070c0e99bd8760 MD5 89119737 2023-07-05 09:27:33 https://researchdata.bath.ac.uk/1255/18/%289H-Fluoren-9-yl%29methyl%202-acetyl-1H-pyrrole-1-carboxylate%20%2816%29.zip 1255 18 18 application/zip other en public cc_by

(9H-Fluoren-9-yl)methyl 2-acetyl-1H-pyrrole-1-carboxylate (16).zip

data 17271 2 61757 document 17271 2,2,2-Trichloroethyl 2-(2-(4-isobutylphenyl)propanoyl)-1H-pyrrole-1-carboxylate (27).zip application/zip d540b2af6023582bb7c75f28a12951f8 MD5 105327555 2023-07-05 09:28:42 https://researchdata.bath.ac.uk/1255/19/2%2C2%2C2-Trichloroethyl%202-%282-%284-isobutylphenyl%29propanoyl%29-1H-pyrrole-1-carboxylate%20%2827%29.zip 1255 19 19 application/zip other en public cc_by

2,2,2-Trichloroethyl 2-(2-(4-isobutylphenyl)propanoyl)-1H-pyrrole-1-carboxylate (27).zip

data 17272 2 61759 document 17272 2-(Trimethylsilyl)ethyl 1H-pyrrole-1-carboxylate (10).zip application/zip 3fb5ae2b4b1be384a98ebc4b4308c6a7 MD5 66763249 2023-07-05 09:29:34 https://researchdata.bath.ac.uk/1255/20/2-%28Trimethylsilyl%29ethyl%201H-pyrrole-1-carboxylate%20%2810%29.zip 1255 20 20 application/zip other en public cc_by

2-(Trimethylsilyl)ethyl 1H-pyrrole-1-carboxylate (10).zip

data 17273 2 61761 document 17273 Benzyl 2-acetyl-1H-pyrrole-1-carboxylate (15).zip application/zip 31ddecbbdcca60cdbf9af5728799251e MD5 67277415 2023-07-05 09:30:07 https://researchdata.bath.ac.uk/1255/21/Benzyl%202-acetyl-1H-pyrrole-1-carboxylate%20%2815%29.zip 1255 21 21 application/zip other en public cc_by

Benzyl 2-acetyl-1H-pyrrole-1-carboxylate (15).zip

data 17274 2 61763 document 17274 2-(Trimethylsilyl)ethyl carbamate.zip application/zip 9eb5532d5bdb1fffed7dfddc422db950 MD5 1595948 2023-07-05 09:30:23 https://researchdata.bath.ac.uk/1255/22/2-%28Trimethylsilyl%29ethyl%20carbamate.zip 1255 22 22 application/zip other en public cc_by

2-(Trimethylsilyl)ethyl carbamate.zip

data 17275 2 61765 document 17275 (2-Acetyl-9H-fluoren-9-yl)methyl 2-acetyl-1H-pyrrole-1-carboxylate (29).zip application/zip aff3e293af619116ab1cf12644cd6d3c MD5 12628817 2023-07-05 09:30:44 https://researchdata.bath.ac.uk/1255/23/%282-Acetyl-9H-fluoren-9-yl%29methyl%202-acetyl-1H-pyrrole-1-carboxylate%20%2829%29.zip 1255 23 23 application/zip other en public cc_by

(2-Acetyl-9H-fluoren-9-yl)methyl 2-acetyl-1H-pyrrole-1-carboxylate (29).zip

data 17276 2 61767 document 17276 ,2,2-Trichloroethyl 2-(4-chlorobutanoyl)-1H-pyrrole-1-carboxylate (21).zip application/zip f1c1b49ed47bfb38855fcef0be58ba5d MD5 9715718 2023-07-05 09:31:07 https://researchdata.bath.ac.uk/1255/24/%2C2%2C2-Trichloroethyl%202-%284-chlorobutanoyl%29-1H-pyrrole-1-carboxylate%20%2821%29.zip 1255 24 24 application/zip other en public cc_by

,2,2-Trichloroethyl 2-(4-chlorobutanoyl)-1H-pyrrole-1-carboxylate (21).zip

data 17277 2 61769 document 17277 2-(4-iso-Butylphenyl)-1-(1H-pyrrol-2-yl)propan-1-one (28).zip application/zip b2c192085af5d98177f65cfbeb49bdcd MD5 68161027 2023-07-05 09:31:41 https://researchdata.bath.ac.uk/1255/25/2-%284-iso-Butylphenyl%29-1-%281H-pyrrol-2-yl%29propan-1-one%20%2828%29.zip 1255 25 25 application/zip other en public cc_by

2-(4-iso-Butylphenyl)-1-(1H-pyrrol-2-yl)propan-1-one (28).zip

data 17278 2 61771 document 17278 Allyl carbamate.zip application/zip e6a4c7753230f62c2a881dbd0e63ee75 MD5 1670371 2023-07-05 09:32:18 https://researchdata.bath.ac.uk/1255/26/Allyl%20carbamate.zip 1255 26 26 application/zip other en public cc_by

Allyl carbamate.zip

data 17279 2 61773 document 17279 2,2,2-Trichloroethyl 3-tetradecanoyl-1H-pyrrole-1-carboxylate (19).zip application/zip 8a20d0d929b9748f56f1670573e468e0 MD5 40775639 2023-07-05 09:32:59 https://researchdata.bath.ac.uk/1255/27/2%2C2%2C2-Trichloroethyl%203-tetradecanoyl-1H-pyrrole-1-carboxylate%20%2819%29.zip 1255 27 27 application/zip other en public cc_by

2,2,2-Trichloroethyl 3-tetradecanoyl-1H-pyrrole-1-carboxylate (19).zip

data 17280 2 61775 document 17280 Methyl 1H-pyrrole-1-carboxylate (8).zip application/zip e89f40b9fcd76959129df28a530c50e8 MD5 1641630 2023-07-05 09:33:23 https://researchdata.bath.ac.uk/1255/28/Methyl%201H-pyrrole-1-carboxylate%20%288%29.zip 1255 28 28 application/zip other en public cc_by

Methyl 1H-pyrrole-1-carboxylate (8).zip

data 17281 2 61777 document 17281 2,2-Diphenyl-1-(1H-pyrrol-3-yl)ethan-1-one (36).zip application/zip 089f23418de3437d962537cb6b80b12b MD5 150702275 2023-07-05 09:34:23 https://researchdata.bath.ac.uk/1255/29/2%2C2-Diphenyl-1-%281H-pyrrol-3-yl%29ethan-1-one%20%2836%29.zip 1255 29 29 application/zip other en public cc_by

2,2-Diphenyl-1-(1H-pyrrol-3-yl)ethan-1-one (36).zip

data archive 12234 disk0/00/00/12/55 2023-08-18 14:06:24 2024-07-10 14:38:36 2023-08-18 14:06:24 data_collection show Hann Jodie jh2585@bath.ac.uk University of Bath TRUE Lewis Simon S.E.Lewis@bath.ac.uk 0000-0003-4555-4907 University of Bath FALSE Lyall Catherine C.L.Lyall@bath.ac.uk 0000-0002-5175-641X University of Bath FALSE Kociok-Kohn Gabriele G.Kociok-Kohn@bath.ac.uk 0000-0002-7186-1399 University of Bath FALSE Dataset for the Synthesis of N-alkoxycarbonyl pyrroles from O-substituted carbamates – A synthetically enabling pyrrole protection strategy CM0030 dept_chem Pyrroles, Synthesis, Protecting groups, acylations, organic chemistry The data are labelled with compound name and number according to paper. This dataset contains nuclear magnetic resonance (NMR) raw data for all novel compounds reported in the associated publication, "Synthesis of N-alkoxycarbonyl pyrroles from O-substituted carbamates – A synthetically enabling pyrrole protection strategy". The NMR files are provided as FID (Free Induction Decay) files, the standard format for NMR raw data. There are multiple software packages that can read this data, including but not limited to MestreNova, TopSpinACD/Labs NMR Workbook suite, ACD/Labs Spectrus JS. 2023-08-18 University of Bath public RightsHolder University of Bath Engineering and Physical Sciences Research Council https://doi.org/10.13039/501100000266 EP/T518013/1 DTP 2020-2021 University of Bath NMR Spectroscopy: 1H and 13C NMR spectra were obtained using a 500 MHz Agilent ProPulse 500 or a 400 MHz Bruker NMR spectrometer, for which proton decoupling was active for 13C NMR. Spectra were acquired at 298 K and were referenced to residual solvent peaks. Chemical shifts are reported in parts per million (ppm) relative to residual chloroform (δ = 7.26 ppm, 1H; 77.16 ppm, 13C), acetone (δ = 2.05 ppm, 1H; 29.84, 206.26 ppm, 13C) or dimethyl sulfoxide (δ = 2.50 ppm, 1H; 39.52 ppm, 13C). Coupling constants, J, reported in Hz, were calculated using MestreNova x64 to the nearest 0.1 Hz. 1H and 13C{1H} assignments for novel compounds are corroborated though 2D NMR experiments (COSY, NOESY, HSQC, HMBC). Further details of the methodology may be found in the associated paper. MestreNova - NMR analysis General procedure for N-Carboxy pyrrole synthesis: Carbamate (4 mmol, 1.0 equiv) and 1,4-dimethoxytetrahydrofuran (0.63 mL, 4.4 mmol, 1.1 equiv, mixture of cis and trans) were added to a flask and purged with nitrogen. AcOH (2.2 mL) was added, and the reaction was heated to reflux (110 °C) using a heating mantle. The reaction was monitored by TLC, and upon completion was cooled to ambient temperature. (Vanillin TLC stain used for non-UV active substrates). CH2Cl2 (50 mL) was added, then washed with saturated Na2CO3(aq) (50 mL × 2), then brine (50 mL). The organic layer was dried over MgSO4 and filtered, then the filtrate was concentrated in vacuo. The crude product was purified by passage through a silica plug (elution with CH2Cl2) and any residual 1,4-dimethoxytetrahydrofuran starting material was removed under vacuum. General Procedure for Acylation reactions using TFAA: To a nitrogen-purged flask of N-carboxy pyrrole (1.0 equiv), and carboxylic acid (3.0 equiv) in dry dichloromethane (c = 0.44 M), trifluoroacetic anhydride (10 equiv.) was added dropwise at ambient temperature. The reaction was monitored by TLC, and upon completion the reaction was diluted with CH2Cl2 and washed with 1 M Na2CO3(aq). The organic layer was separated, and the aqueous layer extracted with CH2Cl2 (×2). The combined organic solutions were then washed with brine, dried over MgSO4, and filtered, then the filtrate was concentrated in vacuo. The crude product was purified by column chromatography (SiO2, EtOAc–Pet Ether). General Procedure for Acylation reactions using Tf2O: To a nitrogen-purged flask of N-carboxy pyrrole (1 equiv.), and carboxylic acid (1 equiv.) in dry dichloromethane (c = 0.44 M), trifluoromethanesulfonic anhydride (10 equiv.) was added dropwise at 0 oC. The reaction was stirred without further cooling and monitored by TLC, and upon completion the reaction was diluted with CH2Cl2 and washed with 1 M Na2CO3 (aq). The organic layer was separated, and the aqueous layer extracted with CH2Cl2 (×2). The combined organic solutions were then washed with brine, dried over MgSO4, and filtered, then the filtrate was concentrated in vacuo. The crude product was purified by column chromatography (SiO2, EtOAc–Pet Ether). General Procedure for N-Troc deprotection: To zinc dust (1.72 mmol) and the N-Troc protected product (0.44 mmol), CH2Cl2 (3.2 mL) and AcOH (0.66 mL) were added. The reaction was stirred at ambient temperature and monitored by TLC until consumption of starting material. The reaction mixture was diluted with acetone (30 mL) and filtered through celite, then concentrated under vacuum to obtain analytically pure product. General Procedure for N-Tosyl deprotection: NaOH pellets (3 equiv.) were crushed and added to a solution of N-Tosyl pyrrole product in (9:1) MeOH/H2O (0.81 M) and stirred overnight at ambient temperature. EtOAc was added, the phases were separated, and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to obtain analytically pure product. en 1 10.15125/BATH-01255 https://doi.org/10.1021/acs.joc.3c01257 pub open Dataset