93779-29-4

Basic information

• Product Name: (S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride
• Synonyms: (1S, 3S, 5S)-2-AZABICYCLO [3.3.0] OCTANE-3-CARBOXYLIC ACID BENZYL ESTER HYDROCHLORIDE;BENZYL 2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLATE HYDROCHLORIDE;(+/-) phenylmethoxy octahydro-cyclopenta[b]pyrrole-2- carboxylate hydrochloride;RACEMIC-2-AZABICYCLO-(3,3,0)-OCTANE-3-CARBOXYLIC ACID BENZYL ESTER HCL;(S,S)-2-AZABICYCLO[3,3,0]-OCTANE-3-CARBOXYLIC ACID BENZYL ESTER HCL;(S,S)-2-AZABICYCLO[3,3,0]OCTANE-3-CARBOXYLIC ACID BENZYL ESTER HYDROCHLORIDE;(R,R,R)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER HYDROCHLORIDE SALT;(+)Benzyl,endo-CIS-2-Azabicyclo[3,3,0]-octane-3-carboxalate mono hydrochloride
• CAS NO: 93779-29-4
• Molecular Formula: C₁₅H₁₉NO₂*ClH
• Molecular Weight: 281.78
• EINECS: 1806241-263-5
• Product Categories: Pharmaceutical Intermediates;INTERMEDIATESOFRAMIPRIL;chiral;Aromatics;Chiral Reagents;Building Blocks;Heterocyclic Building Blocks;Pyrrolidines;NULL
• Mol File: 93779-29-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 178-182 °C(lit.)
• Boiling Point: 390.5 °C at 760 mmHg
• Flash Point: 190 °C
• Appearance: white to light yellow crystal powder
• Vapor Pressure: 1.76E-06mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Ethanol, Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: (S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride(93779-29-4)
• EPA Substance Registry System: (S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride(93779-29-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 93779-29-4(Hazardous Substances Data)

Usage

Description

(S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride is a white to light yellow crystalline powder that serves as an intermediate in the synthesis of Ramipril (R111000(P)), an antihypertensive medication. (S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride plays a crucial role in the production of Ramipril, which is an angiotensin-converting enzyme (ACE) inhibitor and is converted to its active diacid metabolite.

Uses

Used in Pharmaceutical Industry:
(S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride is used as a key intermediate in the synthesis of Ramipril, an antihypertensive drug. It contributes to the development of this medication, which is an ACE inhibitor, helping to regulate blood pressure and provide cardiovascular benefits for patients suffering from hypertension.
As an intermediate in the synthesis of Ramipril, (S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride is essential for the production of a medication that can effectively manage high blood pressure and improve the overall health of individuals with cardiovascular conditions.

InChI:InChI=1/C15H19NO2.ClH/c17-15(18-10-11-5-2-1-3-6-11)14-9-12-7-4-8-13(12)16-14;/h1-3,5-6,12-14,16H,4,7-10H2;1H/t12-,13-,14?;/m0./s1

Upstream product

• 93661-93-9 2,3,3a,4,5,6-Hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid; hydrochloride 
• 87269-85-0 (±)-methyl 2-(acetylamino)-3-(2-oxocyclopentyl)-propionate 
• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 87269-86-1 cis,endo-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride 
• 100-51-6 benzyl alcohol 
• 87269-86-1 (1RS,3RS,5RS)-2-Azabicyclo<3.3.0>octan-3-carbonsaeure-hydrochlorid 
• 765857-50-9 (2S)-2,3,3a,4,5,6-hexahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 87269-86-1 (S,S,S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride 
• 120-92-3 cyclopentanone 
• 109428-53-7 (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 59983-35-6 Cyclopentylidene-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 1296242-98-2 C₁₅H₁₇NO₂ 
• 94569-19-4 2-aza-bicyclo[3.3.0]octane-3-carboxylic acid benzyl ester hydrochloride 
• 1296306-77-8 2-aza-bicyclo[3.3.0]octane-3-carboxylic acid 

Downstream Products

• 87269-87-2 benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride 
• 109428-53-7 (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 87269-88-3 2--L-alanyl>-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester 
• 2387-23-7 1,3-Dicyclohexylurea 
• 135214-79-8 S,S,S-2-azabicyclo[3,3,0]-octane-3-carboxylic acid benzyl ester L-mandelic acid salt 
• 87333-19-5 Ramipril 
• 126110-93-8 (2S,3aS,6aS)-1-((S)-6-Benzyloxycarbonylamino-2-hydroxy-hexanoyl)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester 

Relevant articles and documents

Shape Similarity by Fractal Dimensionality: An Application in the de novo Design of (?)-Englerin A Mimetics

Molecular shape and pharmacological function are interconnected. To capture shape, the fractal dimensionality concept was employed, providing a natural similarity measure for the virtual screening of de novo generated small molecules mimicking the structurally complex natural product (?)-englerin A. Two of the top-ranking designs were synthesized and tested for their ability to modulate transient receptor potential (TRP) cation channels which are cellular targets of (?)-englerin A. Intracellular calcium assays and electrophysiological whole-cell measurements of TRPC4 and TRPM8 channels revealed potent inhibitory effects of one of the computer-generated compounds. Four derivatives of this identified hit compound had comparable effects on TRPC4 and TRPM8. The results of this study corroborate the use of fractal dimensionality as an innovative shape-based molecular representation for molecular scaffold-hopping.

Asymmetric synthesis of (S,S,S)-2-Aza-bicyclo-[3.3.0]-octane-3-carboxylic acid benzyl ester: Formal synthesis of ramipril

An asymmetric synthesis of (S,S,S)-2-aza-bicyclo-[3.3.0]-octane-3- carboxylic acid benzyl ester 2 as an intermediate of angiotensin converting enzyme (ACE) inhibitor, ramipril 1, is described.

METHOD FOR THE PRODUCTION OF RAMIPRIL

An improved method for preparing ramipril is disclosed, and also an intermediate for use in the method.