Carbamic acid, [(1R,3S)-3-aminocyclopentyl]-, 1,1-dimethylethyl ester (9CI)

Base Information

• Chemical Name: Carbamic acid, [(1R,3S)-3-aminocyclopentyl]-, 1,1-dimethylethyl ester (9CI)
• CAS No.: 774212-81-6
• Molecular Formula: C10H20 N2 O2
• Molecular Weight: 200.281
• Mol file: 774212-81-6.mol

Synonyms:Carbamic acid, [(1R,3S)-3-aminocyclopentyl]-, 1,1-dimethylethyl ester (9CI)

Chemical Property of Carbamic acid, [(1R,3S)-3-aminocyclopentyl]-, 1,1-dimethylethyl ester (9CI)

Chemical Property:

• Boiling Point: 304.2±31.0 °C(Predicted)
• PKA: 12.37±0.40(Predicted)
• PSA: 67.84000
• Density: 1.04±0.1 g/cm3(Predicted)
• LogP: 2.29560
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-Butyl((1R,3S)-3-Aminocyclopentyl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl ((1R,3S)-3-Aminocyclopentyl)carbamate is used as a reactant in the synthesis of C-2 hydroxyethyl imidazopyrrolo pyridines as JAK1 inhibitors.

Technology Process of Carbamic acid, [(1R,3S)-3-aminocyclopentyl]-, 1,1-dimethylethyl ester (9CI)

There total 3 articles about Carbamic acid, [(1R,3S)-3-aminocyclopentyl]-, 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: 95.7%

((1R,3S)-3-benzyloxycarbonylamino-cyclopentyl)-carbamic acid tert-butyl ester (774212-79-2,1315495-87-4,881891-89-0) → ((1R,3S)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester (774212-81-6,1197398-99-4,454709-98-9,947732-58-3)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; for 15.5h;

Reference yield: 56.0%

→ ((1R,3S)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester (774212-81-6,1197398-99-4,454709-98-9,947732-58-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; In dichloromethane; at 20 ℃; for 1.5h;

Reference yield:

(1S,3R)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid (261165-05-3) → ((1R,3S)-3-amino-cyclopentyl)-carbamic acid tert-butyl ester (774212-81-6,1197398-99-4,454709-98-9,947732-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; diphenylphosphoranyl azide / toluene / 1 h / 2 °C / Inert atmosphere

1.2: 85 °C / Inert atmosphere

2.1: hydrogen; palladium hydroxide, 20 wt% on carbon / ethanol / 20 °C

With palladium hydroxide, 20 wt% on carbon; diphenylphosphoranyl azide; hydrogen; triethylamine; In ethanol; toluene;

upstream raw materials:

((1R,3S)-3-benzyloxycarbonylamino-cyclopentyl)-carbamic acid tert-butyl ester

(1S,3R)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid

Downstream raw materials:

[(1R,3S)-3-( 1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-cyclopentyl]-carbamic acid tert-butyl ester

(R)-1-(6-benzenesulfonyl-1-[(1S,3R)-3-(2,2-difluoro-ethylamino)-cyclopentyl]-1,6-dihydro-1,3,5,6-tetraaza-as-indacen-2-yl)-ethanol

(R)-1-(6-benzenesulfonyl-1-[(1S,3R)-3-(2,2,2-trifluoro-ethylamino)-cyclopentyl]-1,6-dihydro-1,3,5,6-tetraaza-as-indacen-2-yl)-ethanol

(R)-1-[1-((1S,3R)-3-amino-cyclopentyl)-6-benzenesulfonyl-1,6-dihydro-1,3,5,6-tetraaza-as-indacen-2-yl]-ethanol

Refernces

• 1、 -. "INHIBITORS OF BRUTON'S TYROSINE KINASE AND METHODS OF THEIR USE". Page/Page column 124. . Retrieved 2018/06/30.
• 2、 -. "1,3-DISUBSTITUTED CYCLOPENTANE DERIVATIVES". Page/Page column 65; 66. . Retrieved 2015/02/25.