(2S,3aS,6aS)-Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride

Base Information

• Chemical Name: (2S,3aS,6aS)-Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride
• CAS No.: 87269-87-2
• Molecular Formula: C₁₅H₁₉NO₂*ClH
• Molecular Weight: 281.782
• Hs Code.: 2933990090
• European Community (EC) Number: 617-991-6,618-975-1
• UNII: 38HKS9C1WM
• DSSTox Substance ID: DTXSID501007472
• Mol file: 87269-87-2.mol

Synonyms:87269-87-2;(2S,3aS,6aS)-Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride;benzyl (2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride;Benzyl (S,S,S)-2-azabicyclo[3.3.0]octane-3-carboxylate hydrochloride;38HKS9C1WM;(S,S,S)-2-AZABICYCLO[3,3,0]-OCTANE-3-CARBOXYLIC ACID BENZYL ESTER HYDROCHLORIDE;1279035-95-8;benzyl (2S,3aS,6aS)-1,2,3,3a,4,5,6,6a-octahydrocyclopenta[b]pyrrole-2-carboxylate;hydrochloride;(S,S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzyl ester, HCl;(2S,3aS,6aS)-Octahydrocyclopenta[b]pyrrole-2-carboxylic Acid Phenylmethyl Ester Hydrochloride;(S,S,S)-2-Azabicyclo[3.3.0]octane-3-carboxylic Acid, Benzyl Ester, Hydrochloride;Cyclopenta(b)pyrrole-2-carboxylic acid, octahydro-, phenylmethyl ester, hydrochloride (1:1), (2S,3aR,6aR)-;(2S,3aS,6aS)-octahydro-Cyclopenta[b]pyrrole-2-carboxylic acid, Benzyl Ester, HCl;(S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride;(S,S,S)-2-Azabicyclo[3,3,0]-octane-3-carboxylic acid benzylester hydrochloride;HLXCXOQXUDRJLF-JKBZPBJLSA-N;93779-29-4;UNII-38HKS9C1WM;(1S,3S,5S)-2-Azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride;SCHEMBL1997637;DTXSID501007472;MFCD04974076;MFCD06658210;AKOS015895588;CS-W008300;MG-0725;B5344;EN300-383912;J-502554;Q-200694;(2S,3aS,6aS)-Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate HCl;(2s,3as,6as)-benzyl octahydrocyclopenta[b]pyrrole-2-carboxylatehydrochloride;(2S,3aS,6aS)-Benzyloctahydrocyclopenta[b]pyrrole-2-carboxylatehydrochloride;benzyl (S,S,S)-2-azabicyclo[3,3,0]octane-3-carboxylate. hydrochloride;benzyl (S,S,S)-2-azabicyclo[3,3,0]octane-3-carboxylate.hydrochloride;Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate--hydrogen chloride (1/1);(1S,3S,5S)-2-azabicyclo[3,3,0]-octane-3-3-carboxylic acid benzyl ester hydrochloride;(2S,3AS,6aS)-Benzyl octahydrocyclopenta-[b]pyrrole-2-carboxylate hydrochloride;(2S,3AS,6aS)-Benzyl octahydrocyclopenta-[b]pyrrole-2-carboxylate hydrochloride;(S,S,S)-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;Benzyl (S,S,S)-2-azabicyclo[3.3.0]octane-3-carboxylate hydrochloride, 97%;benzyl(2S,3aS,6aS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride

Chemical Property of (2S,3aS,6aS)-Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride

Chemical Property:

• Appearance/Colour: thick yellow oil
• Vapor Pressure: 1.76E-06mmHg at 25°C
• Melting Point: 176-180 °C(lit.)
• Boiling Point: 390.5 °C at 760 mmHg
• Flash Point: 190 °C
• PSA: 38.33000
• LogP: 3.39120
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Sparingly, Heated), Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 281.1182566
• Heavy Atom Count: 19
• Complexity: 299

Purity/Quality:

99.9% ^*data from raw suppliers

(S,S,S)-2-Azabicyclo[3.3.0]octane-3-carboxylicAcid,BenzylEster,Hydrochloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CC(NC2C1)C(=O)OCC3=CC=CC=C3.Cl
• Isomeric SMILES: C1C[C@H]2C[C@H](N[C@H]2C1)C(=O)OCC3=CC=CC=C3.Cl
• 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.

Technology Process of (2S,3aS,6aS)-Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride

There total 32 articles about (2S,3aS,6aS)-Benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

S,S,S-2-azabicyclo[3,3,0]-octane-3-carboxylic acid benzyl ester L-mandelic acid salt (135214-79-8) → benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride (87269-87-2,87679-25-2,88547-79-9,93779-29-4,94569-19-4,138877-09-5)

Guidance literature:

S,S,S-2-azabicyclo[3,3,0]-octane-3-carboxylic acid benzyl ester L-mandelic acid salt; With sodium hydroxide; In dichloromethane; water; at 25 - 30 ℃;

With hydrogenchloride; In water; isopropyl alcohol;

Reference yield: 80.0%

2-aza-bicyclo[3.3.0]octane-3-carboxylic acid (1296306-77-8,411232-21-8,726691-28-7) + benzyl alcohol (100-51-6,185532-71-2) → 2-aza-bicyclo[3.3.0]octane-3-carboxylic acid benzyl ester hydrochloride (94569-19-4) + benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride (87269-87-2,87679-25-2,88547-79-9,93779-29-4,94569-19-4,138877-09-5)

Guidance literature:

With thionyl chloride; at 0 - 25 ℃; for 13h; Inert atmosphere;

DOI:10.1080/00397911003798757

Reference yield: 70.0%

(2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid (109428-53-7,411232-21-8,726691-28-7) + benzyl alcohol (100-51-6,185532-71-2) → benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride (87269-87-2,87679-25-2,88547-79-9,93779-29-4,94569-19-4,138877-09-5)

Guidance literature:

With hydrogenchloride; thionyl chloride; In 1,4-dioxane; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/cmdc.202000017

upstream raw materials:

(1RS,3RS,5RS)-2-Azabicyclo<3.3.0>octan-3-carbonsaeurebenzylester-hydrochlorid

(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester

benzyl (1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylate

benzyl alcohol

Downstream raw materials:

benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride

(2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid

Ramipril

2--L-alanyl>-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester

Refernces

• 1、 -. "A METHOD FOR PREPARING RAMIPRIL". . . Retrieved 2015/04/15.
• 2、 -. "METHOD FOR THE PRODUCTION OF RAMIPRIL". Page/Page column 6. . Retrieved 2009/01/24.