(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester
• CAS No.: 361440-67-7
• Molecular Formula: C11H18N2O3
• Molecular Weight: 226.276
• Hs Code.: 2933990090
• Mol file: 361440-67-7.mol

Synonyms:Saxagliptin Intermediate; 2-Azabicyclo[3.1.0]hexane-2-carboxylic acid, 3-(aminocarbonyl)-, 1,1-dimethylethyl ester, (1S,3S,5S)-; (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester; (1S,3S,5S)-3-aminocarbonyl-2-azabicyclo[3.1.0]hexane-2-carboxylic acid, 1,1-dimethylethyl ester; (1S,3S,5S)-3-(Amino carbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester; (1S,3S,5S)-tert-Butyl 3-carbamoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate; (1s,3s,5s)-3-(aminocarbonyl)-2-azabicyclo(3.1.0)hexane-2-carboxylic acid tert-butyl

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

Chemical Property:

• Refractive Index: 1.538
• Boiling Point: 388.9 °C at 760 mmHg
• PKA: 16.00±0.20(Predicted)
• Flash Point: 189.024 °C
• PSA: 72.63000
• Density: 1.228 g/cm³
• LogP: 1.50780
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-L-cis-4,5-Methanoprolineamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-L-cis-4,5-Methanoprolineamide is an intermediate used to prepare methanoprolinenitrile-contg. dipeptide mimetics as DPP-IV inhibitors and as antidiabetic agents.

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

There total 20 articles about (1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester 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: 93.0%

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester (709031-38-9) + tetramethylammonium trifluoromethanesulphonate (25628-09-5) → [1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester (361440-67-7)

Guidance literature:

With n-butyllithium; C₄₀H₅₄NiP₂; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 16h; Reagent/catalyst; Solvent; Inert atmosphere;

Reference yield: 84.0%

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (197142-36-2) → [1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester (361440-67-7)

Guidance literature:

(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -15 ℃; for 0.5h;

With ammonia; In tetrahydrofuran; 1,4-dioxane; at -30 - 20 ℃;

DOI:10.1021/jm049924d

Reference yield: 70.0%

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester (709031-38-9) + diiodomethane (75-11-6) → [1S-(1α,3β,5α)]-3-(aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid 1,1-dimethylethyl ester (361440-67-7)

Guidance literature:

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester; diiodomethane; With diethylzinc; In water; ethyl acetate; toluene; at -10 - 0 ℃; for 105h; Inert atmosphere;

With trifluoroacetic acid; In water; ethyl acetate; toluene; at -10 - 16 ℃; for 1.66667h; Reagent/catalyst; Inert atmosphere;

DOI:10.1021/jo500966m

upstream raw materials:

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

(5S)-5-aminocarbonyl-4,5-dihydro-1H-pyrrole-1-carboxylic acid 1-(1,1-dimethylethyl) ester

diiodomethane

di-tert-butyl dicarbonate

Downstream raw materials:

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

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

• 1、 -. "Preparation method of key intermediate of saxagliptin". . . Retrieved 2017/06/02.
• 2、 -. "Protected amino hydroxy adamantane carboxylic acid and process for its preparation". Paragraph 0182; 0183. . Retrieved 2015/11/24.