2-Azabicyclo[3.1.0]hexane-3-carboxamide, (1S,3S,5S)-,monomethanesulfonate

Base Information

• Chemical Name: 2-Azabicyclo[3.1.0]hexane-3-carboxamide, (1S,3S,5S)-,monomethanesulfonate
• CAS No.: 709031-45-8
• Molecular Formula: C6H10N2O.CH4O3S
• Molecular Weight: 222.265
• Hs Code.: 2934999090
• Mol file: 709031-45-8.mol

Synonyms:(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide,methanesulfonic acid

Chemical Property of 2-Azabicyclo[3.1.0]hexane-3-carboxamide, (1S,3S,5S)-,monomethanesulfonate

Chemical Property:

• Vapor Pressure: 0-0Pa at 20-25℃
• PSA: 118.86000
• Density: 1.5g/cm3 at 20℃
• LogP: 1.28540
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

99.9% ^*data from raw suppliers

(1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamidemethanesulfonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Azabicyclo[3.1.0]hexane-3-carboxamide, (1S,3S,5S)-,monomethanesulfonate

There total 7 articles about 2-Azabicyclo[3.1.0]hexane-3-carboxamide, (1S,3S,5S)-,monomethanesulfonate 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: 96.7%

methanesulfonic acid (75-75-2,98527-29-8) + [1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester (361440-67-7) → (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid (709031-45-8)

Guidance literature:

In isopropyl alcohol; at 60 - 70 ℃; for 5h;

Reference yield:

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (194594-23-5) → (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid (709031-45-8)

Guidance literature:

Multi-step reaction with 5 steps

1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine

2: water; lithium hydroxide / ethanol

3: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran

4: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C

5: isopropyl alcohol / 60 °C

With dmap; ammonia; water; diethylzinc; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; lithium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; isopropyl alcohol; 4: |Simmons-Smith Cyclopropanation;

DOI:10.1016/j.bmc.2013.12.061

Reference yield:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide methane sulphonic acid (709031-45-8)

Guidance literature:

Multi-step reaction with 6 steps

1: lithium triethylborohydride / toluene / -70 - -60 °C

2: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine

3: water; lithium hydroxide / ethanol

4: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran

5: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C

6: isopropyl alcohol / 60 °C

With dmap; ammonia; water; diethylzinc; lithium triethylborohydride; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; lithium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; isopropyl alcohol; toluene; 5: |Simmons-Smith Cyclopropanation;

DOI:10.1016/j.bmc.2013.12.061

upstream raw materials:

methanesulfonic acid

[1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

Downstream raw materials:

tert-butyl [(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hex-2-yl]-1-(3-hydroxytricyclo[3.3.1.1³'⁷]dec-1-yl)-2-oxoethyl]carbamate

3-cyano-(αS)-α-(3-hydroxytricyclo[3.3.1.1^3,7]dec-1-yl)-β-oxo-(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-2-ethanecarbamic acid 1,1-dimethylethyl ester

saxagliptin

(R)-3-hydroxyadamantylglycine-L-cis-4,5-methanoprolinenitrile

Refernces

• 1、 Dong, Jizhe,Gong, Yanchun,Liu, Jun,Chen, Xiangfeng,Wen, Xiaoan,Sun, Hongbin. "Synthesis and biological evaluation of all eight stereoisomers of DPP-IV inhibitor saxagliptin". . p. 1383 - 1393. Retrieved 2014/03/21.