(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride - Names and Identifiers

Name	(1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate hydrochloride
Synonyms	Boceprevir InterMediates Boceprevir Intermediate 1 Methyl (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate Methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride (1R,2S,5S)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride (1S,2S,5R)-Methyl 6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate hydrochloride (1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate hydrochloride (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acidmethyl ester hydrochloride (1R,2S,5S)—6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride (1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride (1R,2S,5S)-6,6-Dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid methyl ester hydrochloride (1R,2S,5S)-6,6-Dimethyl-3-Aza-Bicyclo[3.1.0]Hexane-2-Carboxylic Acid Methyl Ester Hydrochloride 3-Azabicyclo[3.1.0]hexane-2-carboxylic acid,6,6-dimethyl-,methyl ester, hydrochloride,(1R,2S,5S)- 3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-diMethyl-, Methyl ester, hydrochloride, (1R,2S,5S)- 3-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 6,6-diMethyl-, Methyl ester, (Hydrochloride), (1R,2S,5S)- (9CI)
CAS	565456-77-1
EINECS	611-400-5

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride - Physico-chemical Properties

Molecular Formula	C9H15NO2.ClH
Molar Mass	205.683
Storage Condition	Inert atmosphere,Room Temperature

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride - Reference Information

Introduction	The intermediate borivir IE (1R,2S,5S)-6, 6-dimethyl-3-azabicyclo [3.1.0] hexane-2-carboxylic acid methyl ester hydrochloride, which is the side chain of boprivir. Borivir is a hepatitis C protease inhibitor developed by Schering-Plough company (Schering-Ploug), which can be used as the main drug of triple therapy (combined with pegylated interferon-α and ribavirin). For the treatment of chronic hepatitis of CHC gene type I. Combined use of the three drugs cured more than 60% of patients, two to three times as much as Recovery Rate of those treated with pegylated interferon-alpha or ribavirin alone, and the treatment time can be shortened while improving by Recovery Rate.
Background	Boceprevir (trade name Boceprevir) chemical name (1S,2S,5S)-N-(4-amino-1-cyclobutyl-3, 4-dioxobutan-2-yl)-3-[(2S)-2-(tert-butylcarbamoylamino)-3, 3-dimethylbutyryl]-6, 6-dimethyl-3-azabicyclo [3.1.0] hexane-2-carboxamide, it is a hepatitis C protease inhibitor developed by Schering-Plough company (Schering-Ploug), which can be used as the main drug of triple therapy (combined with polyethylene glycol a-interferon and ribavirin) for the treatment of chronic hepatitis of CHC gene type I. Combined use of the three drugs cured more than 60% of patients, two to three times as much as Recovery Rate of those treated with pegylated interferon-alpha or ribavirin alone, and the treatment time can be shortened while improving by Recovery Rate. The drug was approved by the U. S. Food and Drug Administration (FDA) on May 13, 2011. 1R, 2S,5S)-6, 6-dimethyl-3-azabicyclo [3.1.0] hexane-2-carboxylic acid methyl ester hydrochloride (I) it is the most cost-effective and key intermediate in the synthesis of the side chain of the drug.
Use	This product is an azabicyclo hexane derivative, which can be used to prepare hepatitis C virus Virus (HCV). NS3 serine protease inhibitor. borivir intermediates are intermediates in organic synthesis and pharmaceutical intermediates, which can be used in laboratory research and development process and chemical production process, mainly as standard and reference substance.
preparation	147.7G of 6, 6-dimethyl-3-azabicyclo [3.1.0] hexane hydrochloride (1.0mol,1.0eq) and 138g potassium carbonate (1.0mol) were added into 1.0 L water, stirred evenly, and then 218.3G di-tert-butyl dicarbonate (mol) was slowly added dropwise under ice bath, the mixture was stirred at room temperature for 3 hours, the stirring was stopped, the liquid separation was allowed to stand, the upper organic layer was separated, the aqueous layer was extracted with methyl tert-butyl ether (MTBE) once, the organic layers were combined, dried with anhydrous sodium sulfate, concentrated to remove the solvent, 205g of Intermediate A were obtained with A yield of 97.0%. To A three-necked flask was added 200g of Intermediate A(0.95mol,1.0eq) followed by 108.5g of (1S,2S)-( )-1, 2-cyclohexanediamine (0.95mol,1.0eq) as chiral ligand, add 2.0L of methyl tert-butyl ether as anhydrous organic solvent, replace three times of air, N2 protection, and cool the flask to -70 ℃ with liquid nitrogen, slowly add Dropwise 0.68L of a solution of SEC-butyllithium cyclohexane having a concentration of 1.4mol/L, wherein the amount of the substance of SEC-butyllithium is 0.95mol(1.0eq), and the addition is completed within 1 hour; the temperature in the reaction flask was controlled not to be greater than -70 ° C., and after stirring for 2H, dried carbon dioxide was introduced for 1H. The reaction system was gradually increased to room temperature, and 2.0L of water was added to the reaction solution, followed by stirring for 10min. The liquid was separated and the aqueous phase was retained, combine three times of the aqueous phase; The aqueous phase with concentrated hydrochloric acid to pH = about 3, using 2.0L methyl tert-butyl ether were extracted three times to obtain organic phase, combined organic phase; The organic phase is dried, Concentration and recrystallization using petroleum ether gave 165g of intermediate B as a white solid in 68.0% yield with an optical purity ee value of 98.0%. 0.65g of intermediate B (1.0 mol, eq) was added to 1.5L of saturated hydrogen chloride methanol solution, heated, refluxed and stirred for 3H, the stirring was stopped, the methanol was removed by rotary evaporation, and recrystallized with petroleum ether, 127g of the intermediate,(1R,2S,5S)-6, 6-dimethyl-3-azabicyclo [3.1.0] hexane-2-carboxylic acid methyl ester hydrochloride, was obtained as a white solid, the yield was 95.0% and the optical purity ee value was 98.5%.

Last Update：2024-04-09 02:00:09

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride

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(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride

(1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate hydrochloride

CAS: 565456-77-1

Molecular Formula: C9H15NO2.ClH

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride - Names and Identifiers

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride - Physico-chemical Properties

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride - Reference Information

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(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride Request for Quotation

(1R,2S,5S)-methyl 6,6-dimethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylate hydrochloride

CAS: 565456-77-1

Molecular Formula: C9H15NO2.ClH

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride - Names and Identifiers

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride - Physico-chemical Properties

(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride - Reference Information

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(1R,2S,5S)-6,6-DiMethyl-3-aza-bicylo[3.1.0]hexane-2-carboxylic acid Methyl ester hydrochloride