L- cis- 4,5- methanoprolinamide HCl

Base Information

• Chemical Name: L- cis- 4,5- methanoprolinamide HCl
• CAS No.: 700376-57-4
• Molecular Formula: C6H10N2O
• Molecular Weight: 126.16
• Mol file: 700376-57-4.mol

Synonyms:saxagliptin Intermediate

Chemical Property of L- cis- 4,5- methanoprolinamide HCl

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.552
• Boiling Point: 331.93°C at 760 mmHg
• PKA: 16.77±0.20(Predicted)
• Flash Point: 154.546°C
• PSA: 55.12000
• Density: 1.238g/cm³
• LogP: 0.25120
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamide is an intermediate used to prepare dipeptidyl peptidase IV (DDP-IV) inhibitors as potential antidiabetes agents.

Technology Process of L- cis- 4,5- methanoprolinamide HCl

There total 1 articles about L- cis- 4,5- methanoprolinamide HCl 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:

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide (700376-57-4) → (1S,3R,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide (700376-57-4)

Guidance literature:

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide; With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 24h; Inert atmosphere;

With di-tert-butyl dicarbonate; In tetrahydrofuran; tert-butyl alcohol; at 25 ℃; for 2h;

With sodium hydroxide; In isopropyl alcohol; at 20 ℃; pH=8; Reagent/catalyst; Temperature;

Reference yield: 89.3%

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.13,7]decane-1-acetic acid (361442-00-4) + (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide (700376-57-4) → 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 (361442-01-5)

Guidance literature:

(αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid; (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide; With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 0 ℃; for 0.5h;

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In ethyl acetate; at 0 - 20 ℃; for 4.5h;

Reference yield:

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide (700376-57-4) → (1S,3R,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide (700376-57-4)

Guidance literature:

(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide; With potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; for 24h; Inert atmosphere;

With di-tert-butyl dicarbonate; In tetrahydrofuran; tert-butyl alcohol; at 25 ℃; for 2h;

With sodium hydroxide; In isopropyl alcohol; at 20 ℃; pH=8; Reagent/catalyst; Temperature;

Downstream raw materials:

C₁₂H₁₁N₃O₂S

saxagliptin

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

Refernces