Methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride, CAS No. 565456-77-1

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565456-77-1

Catalog No. EBD679748

CAS 565456-77-1

Name Methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride

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Basic Information

Synonyms: (1R,2S,5S)-methyl6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylatehydrochloride 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-dimethyl-,methylester,hydrochloride,(1R,2S,5S)- 3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,6,6-dimethyl-,methylester,hydrochloride(1:1),(1R,2S,5S)- (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylicacidmethylesterhydrochloride Methyl(1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylatehydrochloride BoceprevirIntermediate1 (1R,2S,5S)-6,6-Dimethyl-3-Aza-Bicyclo[3.1.0]Hexane-2-CarboxylicAcidMethylEsterHydrochloride (1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylicacidMethylesterhydrochloride Boceprevirintermediate (1R,2S,5S)-Methyl-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylicacidmethylesterHCl

Molecular Formula: C9H16ClNO2

Molecular Weight: 205.68

Categories: Synthetic Chemistry > Organic Building Blocks > Amines Synthetic Chemistry > Organic Building Blocks > Carboxylic Acids and Esters Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates

Product Description:

Methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride is a chiral, bicyclic amine derivative featuring a 3-azabicyclo[3.1.0]hexane core with a methyl ester substituent at the 2-position and a gem-dimethyl group at the 6-position. The hydrochloride salt form enhances its stability and solubility. This compound is primarily utilized as a key chiral intermediate in the synthesis of boceprevir, a hepatitis C virus (HCV) NS3/4A protease inhibitor. Its rigid bicyclic structure and defined stereochemistry (1R,2S,5S) are critical for mimicking the peptide backbone of the viral protease substrate, enabling potent enzyme inhibition. Additionally, it serves as a versatile building block for developing other protease inhibitors and bioactive molecules targeting viral or neurological pathways. The compound is typically stored under inert atmosphere and at low temperatures to prevent hydrolysis of the ester group. Its high enantiopurity and structural complexity make it valuable in medicinal chemistry for constructing constrained peptidomimetics and exploring structure-activity relationships in drug discovery.

Physical Properties