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

Chemical Properties

white to light yellow crystal powde

Uses

rel-(R,R,R)-2-Azabicyclo[3,3,0]-octane-3-carboxylic Acid Benzyl Ester Hydrochloride is an intermeidate in the synthesis of Ramipril (R111000(P)), which is an antihypertensive. Ramipril is an angiotensin converting enzyme (ACE) inhibitor, converts to the active diacid metabolite.

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

• 135214-79-8 S,S,S-2-azabicyclo[3,3,0]-octane-3-carboxylic acid benzyl ester L-mandelic acid salt 
• 87269-86-1 (S,S,S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride 
• 100-51-6 benzyl alcohol 
• 87269-85-0 (±)-methyl 2-(acetylamino)-3-(2-oxocyclopentyl)-propionate 
• 765857-50-9 (2S)-2,3,3a,4,5,6-hexahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 93661-93-9 2,3,3a,4,5,6-Hexahydro-cyclopenta[b]pyrrole-2-carboxylic acid; hydrochloride 
• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 87269-86-1 cis,endo-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride 
• 87269-86-1 (1RS,3RS,5RS)-2-Azabicyclo<3.3.0>octan-3-carbonsaeure-hydrochlorid 
• 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 

Downstream Products

• 93779-32-9 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester 
• 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 
• 87333-19-5 Ramipril 
• 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 

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.

A PROCESS FOR PREPARATION OF RAMIPRIL

Disclosed herein is a process for preparation of Ramipril; which comprises; reacting salts of (S,S,S)-azabicyclo[3.3.0]-octane-3-carboxylate with N-[l-(S)-ethoxy carbonyl)-3- phenyl propyl] -L-alanine in presence of dicyclohexylcarbodimide (DCC) and 1- hydroxybenzotriazole (HOBT) in a suitable solvent medium.