(2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Name:(2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:1218929-66-8
Molecular Formula:C₂₇H₃₂FN₃O₅
Molecular Weight:497.567
Hs Code.:

Synonyms:(2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 11 articles about (2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-hydroxy-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: 93.0%

: 1218929-65-7
(2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 1218929-66-8
(2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 - 45 ℃; for 6h;

Reference yield:

: 187039-57-2,335280-19-8
(2S,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

: 1218929-66-8
(2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 90 °C

2.1: 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C

3.1: lithium borohydride / tetrahydrofuran / 3 h / 0 - 20 °C

4.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C

5.1: triethylamine / 12 h

6.1: thionyl chloride / dichloromethane / 1 h / -78 °C

6.2: 1 h / -78 °C

7.1: / acetonitrile / 16 h / 20 °C

8.1: hydrogen / ethanol / 1.5 h / 2585.81 Torr

9.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 - 45 °C

With 1H-imidazole; lithium borohydride; thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; sulfur trioxide pyridine complex; potassium carbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 156129-73-6
tert-butyl (2R,3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-(hydroxymethyl)pyrrolidine-1-carboxylate

: 1218929-66-8
(2R)-[2-benzyloxycarbonylamino-(1S)-(6-fluoro-1H-indol-3-yl)-ethyl]-(3S)-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C

2.1: triethylamine / 12 h

3.1: thionyl chloride / dichloromethane / 1 h / -78 °C

3.2: 1 h / -78 °C

4.1: / acetonitrile / 16 h / 20 °C

5.1: hydrogen / ethanol / 1.5 h / 2585.81 Torr

6.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 - 45 °C

With thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; sulfur trioxide pyridine complex; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile;