N-Boc-cis-3,4-Methylene D-Proline

Base Information

• Chemical Name: N-Boc-cis-3,4-Methylene D-Proline
• CAS No.: 937244-10-5
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26
• Mol file: 937244-10-5.mol

Synonyms:N-Boc-cis-3,4-Methylene D-Proline;(1S,2R,5R)-3-Azabicyclo[3.1.0]hexane-2,3-dicarboxylic Acid 3-(1,1-DiMethylethyl) Ester

Chemical Property of N-Boc-cis-3,4-Methylene D-Proline

Chemical Property:

• PSA: 66.84000
• LogP: 1.26430

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-cis-3,4-methylene D-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-cis-3,4-Methylene D-Proline is used in the pyrrolidine carboxamides preparation and SAR as 11β-HSD1 inhibitors. Used in the pyrrolidine carboxamides preparation and SAR as 11β-HSD1 inhibitors.

Technology Process of N-Boc-cis-3,4-Methylene D-Proline

There total 8 articles about N-Boc-cis-3,4-Methylene D-Proline 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: 98.0%

(-)-cis-(1S,2R,5R)-2-benzyl 3-tert-butyl 3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate → (+)-cis-(1S,2R,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (937244-10-5,1051393-66-8,72448-25-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 3h;

Reference yield: 37.0%

carbon dioxide (124-38-9,18923-20-1) + tert-butyl 3-azabicyclo[3.1.0]hexane-3-carboxylate → (+)-cis-(1S,2R,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (937244-10-5,1051393-66-8,72448-25-0)

Guidance literature:

tert-butyl 3-azabicyclo[3.1.0]hexane-3-carboxylate; With sec.-butyllithium; (-)-sparteine; In diethyl ether; cyclohexane; at -78 ℃; for 38h; Inert atmosphere;

carbon dioxide; In diethyl ether; cyclohexane; at -68 ℃; for 0.05h;

DOI:10.1021/jo4013282

Reference yield:

rac-cis(1S,2R,5R)-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (1051393-66-8,72448-25-0) → (+)-cis-(1S,2R,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (937244-10-5,1051393-66-8,72448-25-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / Reflux

2: citric acid / water

With citric acid; In water; acetonitrile;

DOI:10.1021/jo4013282

upstream raw materials:

carbon dioxide

rac-cis(1S,2R,5R)-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

tert-butyl 6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate

di-tert-butyl dicarbonate

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