Carbamic acid, (5-cyanopentyl)-, 1,1-dimethylethyl ester (9CI)

Base Information

• Chemical Name: Carbamic acid, (5-cyanopentyl)-, 1,1-dimethylethyl ester (9CI)
• CAS No.: 118110-05-7
• Molecular Formula: C11H20 N2 O2
• Molecular Weight: 212.292
• Mol file: 118110-05-7.mol

Synonyms:Carbamic acid, (5-cyanopentyl)-, 1,1-dimethylethyl ester (9CI)

Chemical Property of Carbamic acid, (5-cyanopentyl)-, 1,1-dimethylethyl ester (9CI)

Chemical Property:

• PSA: 62.12000
• LogP: 2.98598

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbamic acid, (5-cyanopentyl)-, 1,1-dimethylethyl ester (9CI)

There total 5 articles about Carbamic acid, (5-cyanopentyl)-, 1,1-dimethylethyl ester (9CI) 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: 75.0%

ε-<(tert-Butoxycarbonyl)amino>capronamide (85535-56-4) → tert-butyl (5-cyanopentyl)carbamate (118110-05-7)

Guidance literature:

With triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; for 1h; 0 deg C to room temp.,;

DOI:10.1055/s-1988-27538

Reference yield:

6-(tert-butoxycarbonylamino)hexanoic acid (6404-29-1) → tert-butyl (5-cyanopentyl)carbamate (118110-05-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Et₃N, ethyl carbonochloridate, 2.) 20percent aq. NH₃ / 1.) THF, -10 deg C, 20 min., 2.) -10 deg C to room temp., overnight

2: 75 percent / Et₃N, trifluoroacetic anhydride / tetrahydrofuran / 1 h / 0 deg C to room temp.,

With ammonium hydroxide; chloroformic acid ethyl ester; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran;

DOI:10.1055/s-1988-27538

Reference yield:

tert-butyl N-(6-aminohexyl)carbamate (51857-17-1) → tert-butyl (5-cyanopentyl)carbamate (118110-05-7)

Guidance literature:

With copper(l) iodide; oxygen; In dichloromethane; at 20 ℃; for 6h; under 760.051 Torr; Sealed tube;

DOI:10.1002/anie.201609255

upstream raw materials:

ε-<(tert-Butoxycarbonyl)amino>capronamide

di-tert-butyl dicarbonate

6-(tert-butoxycarbonylamino)hexanoic acid

6-aminohexanoic acid

Downstream raw materials:

tert-butyl N-(6-aminohexyl)carbamate

Refernces

• 1、 Xu, Boran,Hartigan, Elizabeth M.,Feula, Giancarlo,Huang, Zheng,Lumb, Jean-Philip,Arndtsen, Bruce A.. "Simple Copper Catalysts for the Aerobic Oxidation of Amines: Selectivity Control by the Counterion". supporting information. p. 15802 - 15806. Retrieved 2016/12/16.