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

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Chemical Name:6-acetoxy-(3R)-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester
CAS No.:1218931-09-9
Molecular Formula:C₂₄H₂₄FN₃O₄
Molecular Weight:437.471
Hs Code.:

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

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

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

There total 15 articles about 6-acetoxy-(3R)-(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: 91.0%

: 1218931-07-7
3-acetoxy-(6R)-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

: 1218931-09-9
6-acetoxy-(3R)-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: 3-acetoxy-(6R)-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 2h;

With sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield:

: 137934-80-6
4-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1218931-09-9
6-acetoxy-(3R)-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: silica gel; sodium iodide / cerium(III) chloride heptahydrate / acetonitrile

1.2: 72 h / 20 °C / Neat (no solvent)

2.1: hydrogen / ethanol; water / 2.5 h / 2585.81 Torr

3.1: triethylamine / dichloromethane / 17 h / 0 - 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C

5.1: pyridine-SO₃ complex; triethylamine / dichloromethane; dimethyl sulfoxide / 3 h / 0 - 20 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

6.2: 4.17 h / -78 °C

7.1: borane-THF / tetrahydrofuran / -30 - 20 °C

7.2: 0 - 20 °C

8.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 2 h / 0 °C

9.1: hydrogen / palladium 10% on activated carbon / methanol / 2.5 h / 2585.81 Torr

9.2: 0.25 h / 80 °C

10.1: triethylamine / dmap / dichloromethane / 0 - 20 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

12.1: triethylamine / dmap / dichloromethane / 0 - 20 °C

13.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C

With borane-THF; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; silica gel; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium iodide; dmap; cerium(III) chloride heptahydrate; palladium 10% on activated carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile;

Reference yield:

: 1218930-82-5
2-[2-amino-1-(6-fluoro-1H-indol-3-yl)-ethyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1218931-09-9
6-acetoxy-(3R)-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: triethylamine / dichloromethane / 17 h / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C

3.1: pyridine-SO₃ complex; triethylamine / dichloromethane; dimethyl sulfoxide / 3 h / 0 - 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

4.2: 4.17 h / -78 °C

5.1: borane-THF / tetrahydrofuran / -30 - 20 °C

5.2: 0 - 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dmap / dichloromethane / 2 h / 0 °C

7.1: hydrogen / palladium 10% on activated carbon / methanol / 2.5 h / 2585.81 Torr

7.2: 0.25 h / 80 °C

8.1: triethylamine / dmap / dichloromethane / 0 - 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

10.1: triethylamine / dmap / dichloromethane / 0 - 20 °C

11.1: trifluoroacetic acid / dichloromethane / 2 h / 0 °C

With borane-THF; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; dmap; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;