tert-butyl 3-(((2S,3R)-2-(benzyloxycarbonyl)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methyl)-1H-indole-1-carboxylate

Base Information

Chemical Name:tert-butyl 3-(((2S,3R)-2-(benzyloxycarbonyl)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methyl)-1H-indole-1-carboxylate
CAS No.:1048039-40-2
Molecular Formula:C₃₄H₃₈N₂O₄
Molecular Weight:538.687
Hs Code.:

Synonyms:tert-butyl 3-(((2S,3R)-2-(benzyloxycarbonyl)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methyl)-1H-indole-1-carboxylate

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Chemical Property of tert-butyl 3-(((2S,3R)-2-(benzyloxycarbonyl)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methyl)-1H-indole-1-carboxylate

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Technology Process of tert-butyl 3-(((2S,3R)-2-(benzyloxycarbonyl)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methyl)-1H-indole-1-carboxylate

There total 1 articles about tert-butyl 3-(((2S,3R)-2-(benzyloxycarbonyl)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methyl)-1H-indole-1-carboxylate 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: 60.0%

: 192189-07-4
tert-butyl 3-iodo-1H-indol-1-carboxylate

: 420840-10-4
(S)-[(but-3-enyl)(1-phenylethyl)amino]acetic acid benzyl ester

: 1048039-40-2
tert-butyl 3-(((2S,3R)-2-(benzyloxycarbonyl)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methyl)-1H-indole-1-carboxylate

Guidance literature:: (S)-[(but-3-enyl)(1-phenylethyl)amino]acetic acid benzyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

With zinc dibromide; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;

tert-butyl 3-iodo-1H-indol-1-carboxylate; With tri tert-butylphosphoniumtetrafluoroborate; palladium diacetate; In tetrahydrofuran; diethyl ether; at 20 ℃; Further stages.;
DOI:10.1021/jo801006a

Reference yield:

: 1048039-40-2
tert-butyl 3-(((2S,3R)-2-(benzyloxycarbonyl)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methyl)-1H-indole-1-carboxylate

: (2S,3R)-3-((1H-indol-3-yl)methyl)-1-benzoylpyrrolidine-2-carboxylic acid trifluoroacetic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogen; palladium 10% on activated carbon / methanol / 168 h / 3750.38 Torr

2.1: triethylamine / dichloromethane / 4 h / 20 °C

2.2: 20 °C

With palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; dichloromethane;
DOI:10.1021/jm401419p

Reference yield:

: 1048039-40-2
tert-butyl 3-(((2S,3R)-2-(benzyloxycarbonyl)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methyl)-1H-indole-1-carboxylate

: (2S,3R)-3-((1H-indol-3-yl)methyl)-1-((2,4-dinitrophenyl)thio)pyrrolidine-2-carboxylic acid trifluoroacetic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogen; palladium 10% on activated carbon / methanol / 168 h / 3750.38 Torr

2.1: sodium hydroxide / 1,4-dioxane / 0.25 h

2.2: 4 h / 20 °C

With palladium 10% on activated carbon; hydrogen; sodium hydroxide; In 1,4-dioxane; methanol;
DOI:10.1021/jm401419p