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

Base Information

• Chemical Name: (1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carbonitrile
• CAS No.: 866083-42-3
• Molecular Formula: C₆H₈N₂
• Molecular Weight: 108.143
• Mol file: 866083-42-3.mol

Synonyms:

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

Chemical Property:

• Boiling Point: 237℃
• Flash Point: 97℃
• PSA: 35.82000
• Density: 1.15
• LogP: 0.58918

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Saxagliptin hydrochloride monohydrate, an anti-diabetic drug can be synthesized using a coupling reaction of (S)-phthalimido-(3-hydroxy-adamantan-1-yl)acetic acid with (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-nitrile followed by removal of the phthalimide protecting group and treatment with HCl.

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

There total 5 articles about (1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carbonitrile 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: 98.7%

(1S,3S,5S)-tert-butyl-3-cyano-2-azabicyclo[3.1.0]hexane-2-carboxylate (361442-57-1) → (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile (866083-42-3)

Guidance literature:

With pyridine; benzenesulfonyl chloride; In tetrahydrofuran; at 20 ℃; for 12h; Solvent;

Reference yield:

tert-butyl (1R,3R,5R)-3-cyano-2-azabicyclo[3.1.0]hexane-2-carboxylate → (1R,3R,5R)-2-azabicyclo[3.1.0]hexane-3-carbonitrile (866083-42-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 2h;

Reference yield:

2,5-dibromo-3-fluoro-thiophene (32431-85-9) + C17H23FN4S → (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile (866083-42-3)

Guidance literature:

With 1-(1-methylethyl)piperazine; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,2-dimethoxyethane; Inert atmosphere;

upstream raw materials:

(1S,3S,5S)-tert-butyl-3-cyano-2-azabicyclo[3.1.0]hexane-2-carboxylate

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

2,5-dibromo-3-fluoro-thiophene

Refernces

• 1、 -. "STEROID DERIVATIVE REGULATORS, METHOD FOR PREPARING THE SAME, AND USES THEREOF". . . Retrieved 2020/12/22.
• 2、 -. "COMPOUNDS". Page/Page column 82. . Retrieved 2015/09/22.