87269-87-2

Basic information

• Product Name: (1S,3S,5S)-2-Azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride
• Synonyms: (3S)-BENZYL ENDO CIS-2-AZABICYCLO (3,3,0)-OCTANE HYDROCHLORIDE;BENZYL (S,S,S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLATE HYDROCHLORIDE;ENDO, CIS-2-AZABICYCLO [3.3.0] OCTANE-3-CARBOXYLIC ACID BENZYL ESTER HYDROCHLORIDE;CIS,ENDO-2-AZABICYCLO[3,3,0]OCTANE-3-CARBOXYLIC ACID BENZYL ESTER HYDROCHLORIDE;(S,S,S)-2-AZABICYCLO[3,3,0]-OCTANE-3-CARBOXYLIC ACID BENZYL ESTER HYDROCHLORIDE;(1S,3S,5S)-2-azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride;(1S, 3S, 5S)-2-Azabicyclo[3,3,0]Octane-3-Carborylic Acid Benzyl Ester hydrochlor;(S,S,S)-2-AZABICYCLO (3,3,0) OCTANE CAR&
• CAS NO: 87269-87-2
• Molecular Formula: C₁₅H₁₉NO₂*ClH
• Molecular Weight: 281.78
• Product Categories: Pharmaceutical Intermediates;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;NULL
• Mol File: 87269-87-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 176-180 °C(lit.)
• Boiling Point: 390.5 °C at 760 mmHg
• Flash Point: 190 °C
• Appearance: thick yellow oil
• Vapor Pressure: 1.76E-06mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Sparingly, Heated), Methanol (Slightly), Water (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: (1S,3S,5S)-2-Azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S,5S)-2-Azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride(87269-87-2)
• EPA Substance Registry System: (1S,3S,5S)-2-Azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride(87269-87-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 87269-87-2(Hazardous Substances Data)

Usage

Uses

Benzyl (S,S,S)-2-azabicyclo[3.3.0]octane-3-carboxylate hydrochloride can be used:In the preparation of ramipril, an angiotensin-converting enzyme (ACE) inhibitor.As a starting material for the synthesis of octahydrocyclopenta[b]pyrrole-2-carbonitrile derivatives as potent DPP4 inhibitors.

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

• 87269-87-2 (1RS,3RS,5RS)-2-Azabicyclo<3.3.0>octan-3-carbonsaeurebenzylester-hydrochlorid 
• 93779-32-9 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester 
• 93779-31-8 benzyl (1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylate 
• 100-51-6 benzyl alcohol 
• 135214-79-8 S,S,S-2-azabicyclo[3,3,0]-octane-3-carboxylic acid benzyl ester L-mandelic acid salt 
• 765857-50-9 C₈H₁₁NO₂ 
• 1296306-77-8 2-aza-bicyclo[3.3.0]octane-3-carboxylic acid 
• 94569-19-4 2-aza-bicyclo[3.3.0]octane-3-carboxylic acid benzyl ester hydrochloride 
• 1296242-98-2 C₁₅H₁₇NO₂ 
• 59983-35-6 Cyclopentylidene-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 109428-53-7 (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 120-92-3 cyclopentanone 
• 87269-86-1 (S,S,S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride 
• 87269-85-0 (±)-methyl 2-(acetylamino)-3-(2-oxocyclopentyl)-propionate 

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 
• 918414-52-5 (2S,5aS,6aS)-2-hydroxymethyl-hexahydro-cyclopenta[b]pyrrole-1-carboxylic acid tert-butyl ester 
• 126110-93-8 (2S,3aS,6aS)-1-((S)-6-Benzyloxycarbonylamino-2-hydroxy-hexanoyl)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester 
• 93779-32-9 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-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.