3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

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Chemical Name:3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester
CAS No.:1218930-03-0
Molecular Formula:C₂₂H₂₂FN₃O₂
Molecular Weight:379.434
Hs Code.:

Synonyms:3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

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Chemical Property of 3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

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Technology Process of 3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

There total 13 articles about 3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1218936-08-3
(3aR,6aR)-6S-(6-fluoro-1H-indol-3-yl)-octahydro-pyrrolo[3,2-b]pyrrole-1,3,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester

: 1218930-03-0
3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: (3aR,6aR)-6S-(6-fluoro-1H-indol-3-yl)-octahydro-pyrrolo[3,2-b]pyrrole-1,3,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

With sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield:

: 850003-05-3
(2S,3S)-N-tert-butyloxycarbonyl-3-(tert-butyldimethylsilyloxy)-2-pyrrolidinecarboxylic acid methyl ester

: 1218930-03-0
3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C

2.1: pyridine-SO₃ complex; triethylamine / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C

3.1: triethylamine / 12 h

3.2: 1 h / -78 °C

3.3: 1 h / -78 °C

4.1: / acetonitrile / 40 °C

4.2: 16 h / 20 °C / Neat (no solvent)

5.1: hydrogen / ethanol / 1.5 h / 2585.81 Torr

6.1: triethylamine / dichloromethane / 0 - 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 45 °C

8.1: dmap / dichloromethane / 0 °C

9.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With lithium borohydride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; dmap; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 757247-71-5
tert-butyl (2S,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-formylpyrrolidine-1-carboxylate

: 1218930-03-0
3-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine / 12 h

1.2: 1 h / -78 °C

1.3: 1 h / -78 °C

2.1: / acetonitrile / 40 °C

2.2: 16 h / 20 °C / Neat (no solvent)

3.1: hydrogen / ethanol / 1.5 h / 2585.81 Torr

4.1: triethylamine / dichloromethane / 0 - 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 - 45 °C

6.1: dmap / dichloromethane / 0 °C

7.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With tetrabutyl ammonium fluoride; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; dmap; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;