(2S,3R)-1-tert-Butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,3R)-1-tert-Butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid
• CAS No.: 462123-81-5
• Molecular Formula: C₁₆H₂₇NO₄
• Molecular Weight: 297.395
• Mol file: 462123-81-5.mol

Synonyms:(2S,3R)-1-tert-Butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid

Chemical Property of (2S,3R)-1-tert-Butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1-tert-Butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid

There total 5 articles about (2S,3R)-1-tert-Butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid 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:

cyclohexylmagnesium bromide (931-50-0) → (2S,3R)-1-tert-Butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid (462123-81-5,1449586-26-8)

Guidance literature:

Multi-step reaction with 4 steps

1: chloro-trimethyl-silane; (methylsulfonyl)methane-bromo copper / 2 h / -78 - 20 °C

2: dimethylsulfide borane complex / tetrahydrofuran / 1 h / Reflux

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

4: chromium(VI) oxide; sulfuric acid; water / acetone / 5 h / 20 °C

With chromium(VI) oxide; chloro-trimethyl-silane; dimethylsulfide borane complex; sulfuric acid; (methylsulfonyl)methane-bromo copper; tetrabutyl ammonium fluoride; water; In tetrahydrofuran; acetone;

DOI:10.1016/j.bmc.2011.08.020

Reference yield:

(2S,3R)-3-cyclohexyl-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1344158-18-4) → (2S,3R)-1-tert-Butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid (462123-81-5,1449586-26-8)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; water; In acetone; at 20 ℃; for 5h;

DOI:10.1016/j.bmc.2011.08.020

Reference yield:

(2S,3R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-cyclohexyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (1344158-05-9) → (2S,3R)-1-tert-Butoxycarbonyl-3-cyclohexylpyrrolidine-2-carboxylic acid (462123-81-5,1449586-26-8)

Guidance literature:

Multi-step reaction with 3 steps

1: dimethylsulfide borane complex / tetrahydrofuran / 1 h / Reflux

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

3: chromium(VI) oxide; sulfuric acid; water / acetone / 5 h / 20 °C

With chromium(VI) oxide; dimethylsulfide borane complex; sulfuric acid; tetrabutyl ammonium fluoride; water; In tetrahydrofuran; acetone;

DOI:10.1016/j.bmc.2011.08.020

upstream raw materials:

(2S,3R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-cyclohexyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,3R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-cyclohexyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,3R)-3-cyclohexyl-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(2S,3R)-3-cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester

(S)-3-((S)-2-acetamido-3-methylbutanamido)-4-(((S)-1-((2S,3R)-3-cyclohexyl-2-(((2S,3S)-2-hydroxy-5-oxotetrahydrofuran-3-yl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-4-oxobutanoic acid

(2S,3R)-3-Cyclohexyl-pyrrolidine-2-carboxylic acid