4-(tert-butyl-dimethyl-silanyloxy)-2-[1-(6-fluoro-1H-indol-3-yl)-2-nitro-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Name:4-(tert-butyl-dimethyl-silanyloxy)-2-[1-(6-fluoro-1H-indol-3-yl)-2-nitro-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:1218930-81-4
Molecular Formula:C₂₅H₃₈FN₃O₅Si
Molecular Weight:507.678
Hs Code.:

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

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Chemical Property of 4-(tert-butyl-dimethyl-silanyloxy)-2-[1-(6-fluoro-1H-indol-3-yl)-2-nitro-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of 4-(tert-butyl-dimethyl-silanyloxy)-2-[1-(6-fluoro-1H-indol-3-yl)-2-nitro-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 1 articles about 4-(tert-butyl-dimethyl-silanyloxy)-2-[1-(6-fluoro-1H-indol-3-yl)-2-nitro-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl 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: 75.0%

: 399-51-9
6-fluoro-1H-indole

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

: 1218930-81-4
4-(tert-butyl-dimethyl-silanyloxy)-2-[1-(6-fluoro-1H-indol-3-yl)-2-nitro-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: 6-fluoro-1H-indole; 4-(tert-butyl-dimethyl-silanyloxy)-2-(2-nitro-vinyl)-pyrrolidine-1-carboxylic acid tert-butyl ester; With silica gel; sodium iodide; cerium(III) chloride heptahydrate; In acetonitrile;

at 20 ℃; for 72h; Neat (no solvent);

Reference yield:

: 1218930-81-4
4-(tert-butyl-dimethyl-silanyloxy)-2-[1-(6-fluoro-1H-indol-3-yl)-2-nitro-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

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

Guidance literature:: Multi-step reaction with 11 steps

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

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

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4.5 h / 20 °C

4.1: pyridine-SO₃ complex; triethylamine / dimethyl sulfoxide / 4.5 h / 0 - 20 °C

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

5.2: 5.17 h / -78 °C

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

6.2: 0 - 20 °C

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

8.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; methanol / 4.5 h / 2585.81 Torr

9.1: triethylamine / dmap / dichloromethane / 8 h / 0 - 20 °C

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

11.1: trifluoroacetic acid / dichloromethane / 2.5 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; ethanol; dichloromethane; water; dimethyl sulfoxide;

Reference yield:

: 1218930-81-4
4-(tert-butyl-dimethyl-silanyloxy)-2-[1-(6-fluoro-1H-indol-3-yl)-2-nitro-ethyl]-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 12 steps

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

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

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

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

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

5.2: 4.17 h / -78 °C

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

6.2: 0 - 20 °C

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

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

8.2: 0.25 h / 80 °C

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

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

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

12.1: 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; ethanol; dichloromethane; water; dimethyl sulfoxide;