672325-23-4

Basic information

• Product Name: 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-dimethyl-,methylester,(1R,2S,5S)-(9CI)
• Synonyms: 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-dimethyl-,methylester,(1R,2S,5S)-(9CI);(1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester;(1R,2S,5S)—6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester;3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-diMethyl-, Methyl ester, (1R,2S,5S)-;3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-diMethyl-,Methylester,(1R,2S,5S)-(9C1);3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-diMethyl-,Methylester,(1R,2S,5S)-(9C1) free base
• CAS NO: 672325-23-4
• Molecular Formula: C₉H₁₅NO₂
• Molecular Weight: 169.22
• Product Categories: GLYCINESCAFFOLD;PYRROLE
• Mol File: 672325-23-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 210℃
• Flash Point: 81℃
• Appearance: /
• Density: 1.060
• PKA: 9.40±0.60(Predicted)
• CAS DataBase Reference: 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-dimethyl-,methylester,(1R,2S,5S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-dimethyl-,methylester,(1R,2S,5S)-(9CI)(672325-23-4)
• EPA Substance Registry System: 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-dimethyl-,methylester,(1R,2S,5S)-(9CI)(672325-23-4)

Safety Data

• Hazardous Substances Data: 672325-23-4(Hazardous Substances Data)

Usage

General Description

3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-dimethyl-, methyl ester, (1R,2S,5S)-(9CI) is a chemical compound with a complex structure and a systematic name that indicates its stereochemistry. 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-dimethyl-,methylester,(1R,2S,5S)-(9CI) is an ester derivative of a 3-azabicyclo[3.1.0]hexane-2-carboxylic acid, which is a bicyclic organic compound. The specific stereochemistry indicated by the (1R,2S,5S) designation points to the arrangement of the substituents around the chiral centers in the molecule. 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-dimethyl-,methylester,(1R,2S,5S)-(9CI) may have potential applications in organic synthesis, pharmaceuticals, or other chemical industries, but its exact uses and properties would depend on further research and testing.

Upstream product

• 943516-54-9 6,6-dimethyl-3-azabicyclo[3.1.0]hexane 
• 67-56-1 methanol 
• 1037559-82-2 (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carbonitrile 
• 911835-76-2 (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 

Downstream Products

• 394735-26-3 (1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyryl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester 
• 394735-24-1 (1R,2S,5S)-3-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid methyl ester 
• 951789-91-6 C₂₃H₃₈N₂O₅ 

Relevant articles and documents

Efficient, chemoenzymatic process for manufacture of the boceprevir bicyclic [3.1.0]proline intermediate based on amine oxidase-catalyzed desymmetrization

The key structural feature in Boceprevir, Merck's new drug treatment for hepatitis C, is the bicyclic [3.1.0]proline moiety "P2". During the discovery and development stages, the P2 fragment was produced by a classical resolution approach. As the drug candidate advanced through clinical trials and approached regulatory approval and commercialization, Codexis and Schering-Plough (now Merck) jointly developed a chemoenzymatic asymmetric synthesis of P2 where the net reaction was an oxidative Strecker reaction. The key part of this reaction sequence is an enzymatic oxidative desymmetrization of the prochiral amine substrate.

PROCESS AND INTERMEDIATES FOR THE PREPARATION OF (1R,2S,5S)-6,6-DIMETHYL-3-AZABICYCLO[3,1,0]HEXANE-2-CARBOXYLATES OR SALTS THEREOF

In one embodiment, the present application relates to a process of making a compound of Formula (I); and to certain intermediate compounds that are made within the process of making the compound Formula (I).