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

Base Information

• Chemical Name: Carbamic acid, [(1S,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI)
• CAS No.: 167465-99-8
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.266
• Mol file: 167465-99-8.mol

Synonyms:Carbamic acid, [(1S,3R)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI);[(1S,3R)-3-Hydroxycyclopentyl]carbamic acid tert-butyl ester;(1R,3S)-3-aminocyclopentan-1-ol;(1S,3R)-tert-butyl(3-hydroxycyclopentyl)catbaMte;cis-tert-butyl-3-hydroxycyclopentylcarbamate

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

Chemical Property:

• Boiling Point: 321℃
• PKA: 12.27±0.40(Predicted)
• Flash Point: 148℃
• PSA: 58.56000
• Density: 1.08
• LogP: 1.81540
• Storage Temp.: 2-8°C

Purity/Quality:

99.9% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 17 articles about Carbamic acid, [(1S,3R)-3-hydroxycyclopentyl]-, 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: 95.3%

1-[(3S,1R)-3-N-BOC-aminocyclopentyl]-1-ethanone (204913-01-9) → (1S,3R)-3-hydroxycyclopentyl-1-carbamic acid tert-butyl ester (167465-99-8,1154870-59-3,207729-04-2)

Guidance literature:

1-[(3S,1R)-3-N-BOC-aminocyclopentyl]-1-ethanone; With carbamide peroxide; trifluoroacetic anhydride; In tetrahydrofuran; at 0 ℃; for 7h; Inert atmosphere;

With water; sodium hydroxide; In ethanol; at 10 - 20 ℃; for 5h; Reagent/catalyst; Temperature;

Reference yield: 91.0%

C10H17NO3 → (1S,3R)-3-hydroxycyclopentyl-1-carbamic acid tert-butyl ester (167465-99-8,1154870-59-3,207729-04-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃; for 48h;

Reference yield: 90.0%

Acetic acid (1R,3S)-3-tert-butoxycarbonylamino-cyclopentyl ester (225641-82-7) → (1S,3R)-3-hydroxycyclopentyl-1-carbamic acid tert-butyl ester (167465-99-8,1154870-59-3,207729-04-2)

Guidance literature:

With lithium hydroxide; In methanol; at 25 ℃; for 12h;

upstream raw materials:

vinyl acetate

di-tert-butyl dicarbonate

Acetic acid (1R,3S)-3-tert-butoxycarbonylamino-cyclopentyl ester

tert-Butyl N-hydroxycarbamate

Downstream raw materials:

(1R,3S)-3-amino-1-cyclopentanol hydrochloride

Refernces

• 1、 -. "Preparation method of (1R, 3S)-3-amino-1-cyclopentanol hydrochloride". Paragraph 0025-0026. . Retrieved 2019/12/29.
• 2、 -. "Intermediate for preparing bictegravir and preparation method thereof". . . Retrieved 2019/01/08.