(1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

Base Information

• Chemical Name: (1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
• CAS No.: 400720-05-0
• Molecular Formula: C11H17 N O4
• Molecular Weight: 227.26
• European Community (EC) Number: 883-662-0
• DSSTox Substance ID: DTXSID00585529
• Nikkaji Number: J3.262.062K
• Mol file: 400720-05-0.mol

Synonyms:400720-05-0;(1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid;72448-25-0;(1S,2S,5R)-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid;(1S,2S,5R)-3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid;(1S,2S,5R)-rel-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid;(1S,2S,5R)-3-Boc-3-azabicyclo[3.1.0]hexane-2-carboxylic acid;MFCD08460285;SCHEMBL384513;DTXSID00585529;rac-(1R,2R,5S)-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid;AKOS022184245;[1S-, 2R-, 5R-]3-AZA-BICYCLO[3.1.0]HEXANE-2,3-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER;(1S,2S,5R)-rel-3-Boc-3-azabicyclo[3.1.0]hexane-2-carboxylic acid;AS-36318;CS-0053569;EN300-33652;P17314;P19131;EN300-6499834;Z228589602;REL-(1S,2S,5R)-3-BOC-3-AZABICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID;(1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylicacid;(1S,2S,5R)-3-AZa-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 3-tert-butyl ester

Chemical Property of (1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

Chemical Property:

• Melting Point: 263-265 °C(Solv: water (7732-18-5); acetone (67-64-1))
• Boiling Point: 355.9±25.0 °C(Predicted)
• PKA: 4.03±0.20(Predicted)
• PSA: 66.84000
• Density: 1.276±0.06 g/cm3(Predicted)
• LogP: 1.26430
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 333

Purity/Quality:

99% ^*data from raw suppliers

(1S,2S,5R)-3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC2CC2C1C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H]2C[C@@H]2[C@H]1C(=O)O

Technology Process of (1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

There total 8 articles about (1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 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: 80.0%

(-)-trans-(1S,2S,5R)-2-benzyl 3-tert-butyl 3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate → (-)-trans-(1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (400720-05-0,1051393-66-8,72448-25-0)

Guidance literature:

With palladium 10% on activated carbon; In ethyl acetate; at 20 ℃; for 9h; under 760.051 Torr;

DOI:10.1021/jo4013282

Reference yield:

(1S,2S,5R)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid + di-tert-butyl dicarbonate (24424-99-5) → (-)-trans-(1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (400720-05-0,1051393-66-8,72448-25-0)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/jm301177j

Reference yield:

tert-butyl 3-azabicyclo[3.1.0]hexane-3-carboxylate → (-)-trans-(1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (400720-05-0,1051393-66-8,72448-25-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3,7-dipropyl-7-aza-3-azoniabicyclo[3.3.1]nonane; sec.-butyllithium / tetrahydrofuran; cyclohexane / 1.25 h / -80 - -57 °C / Flow reactor; Inert atmosphere

1.2: -57 - -47 °C / Flow reactor

1.3: 0.75 h / Flow reactor

2.1: ethyl acetate; water / 0.17 h / 70 °C

3.1: potassium hydrogensulfate / ethyl acetate; water

With 3,7-dipropyl-7-aza-3-azoniabicyclo[3.3.1]nonane; potassium hydrogensulfate; sec.-butyllithium; In tetrahydrofuran; cyclohexane; water; ethyl acetate;

DOI:10.1021/jo4013282

upstream raw materials:

di-tert-butyl dicarbonate

rac-cis(1S,2R,5R)-3-[(tert-butoxy)carbonyl]-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

(trans)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

Downstream raw materials:

(1R,4S,5S)-N-[[5-chloro-2-(tetrazol-1-yl)phenyl]methyl]-3-[(2R)-2-hydroxy-3-pyrazol-1-ylpropanoyl]-3-azabicyclo[3.1.0]hexane-4-carboxamide

(1S,2S,5R)-3-((R)-3-tert-butoxy-2-hydroxypropionyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide

(1S,2S,5R)-3-((R)-3-cyclopropyl-2-hydroxypropionyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide

(1S,2S,5R)-3-((R)-2-cyclohexyl-2-hydroxyacetyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 5-chloro-2-tetrazol-1-ylbenzylamide

Refernces

• 1、 Yu, Li-Fang,Eaton, J. Brek,Fedolak, Allison,Zhang, Han-Kun,Hanania, Taleen,Brunner, Dani,Lukas, Ronald J.,Kozikowski, Alan P.. "Discovery of highly potent and selective α4β2-nicotinic acetylcholine receptor (nAChR) partial agonists containing an isoxazolylpyridine ether scaffold that demonstrate antidepressant-like activity. Part II". . p. 9998 - 10009. Retrieved 2013/01/16.