(2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 83487-17-6
• Molecular Formula: C₈H₁₃NO₅
• Molecular Weight: 203.195
• Mol file: 83487-17-6.mol

Synonyms:(2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

Chemical Property of (2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester

There total 2 articles about (2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl 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: 94.0%

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) + methyl chloroformate (79-22-1) → (2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (83487-17-6)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water;

DOI:10.1021/acs.joc.5b00932

Reference yield: 13.0%

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) + methyl chloroformate (79-22-1) → (2S,4R)-dimethyl 4-(methoxycarbonyloxy)pyrrolidine-1,2-dicarboxylate (1415906-44-3) + (2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (83487-17-6)

Guidance literature:

L-4-hydroxyproline methyl ester hydrochloride; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;

methyl chloroformate; In dichloromethane; at 0 - 50 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.10.076

Reference yield: 67.0%

3,6-bis(trifluoromethyl)bromobenzene (328-70-1) + (2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester (83487-17-6) → (6R,7aS)-1,1-bis[3,5-bis(trifluoromethyl)phenyl]-6-hydroxytetrahydropyrrolo[1,2-c]oxazol-3(1H)-one (1360588-94-8)

Guidance literature:

3,6-bis(trifluoromethyl)bromobenzene; With magnesium; In tetrahydrofuran; at 0 ℃; for 1h; Reflux;

(2S,4R)-(-)-N-methyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester; In tetrahydrofuran; at 0 ℃; for 2h; Reflux;

DOI:10.1002/cctc.201300097

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

methyl chloroformate

Downstream raw materials:

(6R,7aS)-1,1-bis[3,5-bis(trifluoromethyl)phenyl]-6-hydroxytetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

(6S,7aS)-6-azido-1,1-bis[3,5-bis(trifluoromethyl)phenyl]tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one

C₃₀H₃₀F₁₂N₂O₂

C₃₄H₃₈F₁₂N₂O₂