Carbamic acid, [(1R,2S)-2-hydroxycyclohexyl]-, phenylmethyl ester

Base Information

• Chemical Name: Carbamic acid, [(1R,2S)-2-hydroxycyclohexyl]-, phenylmethyl ester
• CAS No.: 187333-96-6
• Molecular Formula: C14H19NO3
• Molecular Weight: 249.30600
• DSSTox Substance ID: DTXSID00453537
• Nikkaji Number: J1.033.949I
• Wikidata: Q82274692
• Mol file: 187333-96-6.mol

Synonyms:187333-96-6;Carbamic acid, [(1R,2S)-2-hydroxycyclohexyl]-, phenylmethyl ester;Benzyl N-[(1R,2S)-2-hydroxycyclohexyl]carbamate;rel-[(1R,2S)-2-Hydroxycyclohexyl]carbamic Acid Phenylmethyl Ester;415692-85-2;SCHEMBL5749471;DTXSID00453537;EN300-28278494;[(1beta)-2beta-Hydroxycyclohexyl]carbamic acid benzyl ester

Chemical Property of Carbamic acid, [(1R,2S)-2-hydroxycyclohexyl]-, phenylmethyl ester

Chemical Property:

• PSA: 62.05000
• LogP: 2.42070
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 249.13649347
• Heavy Atom Count: 18
• Complexity: 264

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)NC(=O)OCC2=CC=CC=C2)O
• Isomeric SMILES: C1CC[C@@H]([C@@H](C1)NC(=O)OCC2=CC=CC=C2)O

Technology Process of Carbamic acid, [(1R,2S)-2-hydroxycyclohexyl]-, phenylmethyl ester

There total 11 articles about Carbamic acid, [(1R,2S)-2-hydroxycyclohexyl]-, phenylmethyl 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:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + cis-2-amino-1-cyclohexanol hydrochloride → (1S,2R)-2-(benzyloxycarbonylamino)cyclohexan-1-ol (187333-96-6) + (1S,2R-2-hydroxy-cyclohexyl)-carbamic acid benzyl ester (187334-05-0)

Guidance literature:

With sodium hydrogencarbonate; In water; at 20 ℃; for 6h;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + (1S,2R)-2-(tert-butoxycarbonylamino)cyclohexan-1-ol (291533-28-3,477584-30-8) → (1S,2R)-2-(benzyloxycarbonylamino)cyclohexan-1-ol (187333-96-6)

Guidance literature:

(1S,2R)-2-(tert-butoxycarbonylamino)cyclohexan-1-ol; With hydrogenchloride; In diethyl ether; at 25 ℃; for 21h;

benzyl chloroformate; With sodium hydrogencarbonate; In dichloromethane; water; at 25 ℃; for 3h; Further stages.;

DOI:10.1021/ja001098k

Reference yield:

(+/-)-cis-benzyl N-(2-hydroxycyclohexyl)carbamate (92645-06-2,134070-85-2,134108-76-2) → (1S,2R)-2-(benzyloxycarbonylamino)cyclohexan-1-ol (187333-96-6) + (1S,2R-2-hydroxy-cyclohexyl)-carbamic acid benzyl ester (187334-05-0)

Guidance literature:

With 2,3,5-trimethyl-pyridine; 6-(2-C₁₀H₇-CH₂)-1-(py-4-yl)octahydrocyclopenta[b]pyrrol-6-ol; 2-Methylpropionic anhydride; In dichloromethane; at 20 ℃; for 5h; Title compound not separated from byproducts.;

DOI:10.1039/b108753c

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

cis-2-amino-cyclohexanol

sodium [(benzyloxy)carbonyl]chloroamide

cyclohexene

Downstream raw materials:

(1S,2R)-2-amino-cyclohexan-1-ol formate

Refernces

• 1、 Dehli, Juan R.,Gotor, Vicente. "Dynamic kinetic resolution of 2-oxocycloalkanecarbonitriles: Chemoenzymatic syntheses of optically active cyclic β- and γ-amino alcohols". . p. 6816 - 6819. Retrieved 2007/10/03.
• 2、 Ohkuma, Takeshi,Ishii, Dai,Takeno, Hiroshi,Noyori, Ryoji. "Asymmetric hydrogenation of amino ketones using chiral RuCl2(diphophine)(1,2-diamine) complexes [12]". . p. 6510 - 6511. Retrieved 2007/10/03.