141553-09-5

Basic information

• Product Name: (1R, 2R)-2-Benzylamino-1-cyclohexanol
• Synonyms: (1R, 2R)-2-Benzylamino-1-cyclohexanol;(1R,2R)-2-(benzylaMino)cyclohexan-1-ol;-2-(Benzylamino);(1R,2R)-2-Benzylamino-1-cyclohexanol,99%e.e.;(1R,2R)-2-Benzylamino-1-cyclohexanol, min. 98%
• CAS NO: 141553-09-5
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.29606
• Product Categories: CHIRAL CHEMICALS
• Mol File: 141553-09-5.mol
• Article Data: 40

Chemical Properties

• Appearance: white to light-yellow/Powder
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: (1R, 2R)-2-Benzylamino-1-cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R, 2R)-2-Benzylamino-1-cyclohexanol(141553-09-5)
• EPA Substance Registry System: (1R, 2R)-2-Benzylamino-1-cyclohexanol(141553-09-5)

Safety Data

• Hazardous Substances Data: 141553-09-5(Hazardous Substances Data)

Usage

General Description

(1R, 2R)-2-Benzylamino-1-cyclohexanol is a chemical compound that belongs to the class of cyclohexanols. It is also known as benzylaminocyclohexanol or 1-amino-2-(phenylmethyl)cyclohexanol. (1R, 2R)-2-Benzylamino-1-cyclohexanol has two stereoisomers, (1R, 2R) and (1S, 2S), with the former being the naturally occurring form. It is commonly used as a chiral auxiliary in asymmetric synthesis and as a building block in the preparation of various pharmaceuticals and biologically active compounds. Additionally, it has been studied for its potential as a chiral ligand in catalytic reactions and as a precursor in the synthesis of chiral drugs.

Upstream product

• 40571-86-6 rac-(1R,2R)-2-(benzylamino)cyclohexanol 
• 286-20-4 cyclohexene oxide 
• 100-46-9 benzylamine 
• 38898-70-3 cis-2-amino-cyclohexanol-⁽¹⁾ 
• 100-52-7 benzaldehyde 
• 286-20-4 cyclohexane-1,2-epoxide 
• 98454-42-3 (±)-trans-2-(benzyloxy)cyclohexanamine 
• 882409-01-0 (S)-mandelic acid salt of (1R,2R)-2-trans-2-(benzylamino)cyclohexanol 
• 496924-15-3 (1R,2R)-2-{[1-Phenyl-meth-(E)-ylidene]-amino}-cyclohexanol 
• 5456-63-3 trans-2-aminocyclohexanol hydrochloride 
• 125582-79-8 C₁₉H₃₅NPb 
• 6628-80-4 trans-2-chlorocyclohexanol 
• 109309-80-0 (+/-)-N-benzyl-N-(trans-2-hydroxy-cyclohexyl)-benzamide 
• 931-15-7 (1R,2R)-2-aminocyclohexanol 

Downstream Products

• 496924-13-1 (1R,2R)-trans-2-(N-benzoyl-N-benzyl)amino-1-cyclohexanol 
• 24417-01-4 7-Benzyl-7-aza-bicyclo[4.1.0]heptane 
• 40571-86-6 (+/-)-trans-2-(benzylamino)cyclohexanol 
• 322407-34-1 (1S,2S)-trans-2-(N-benzyl)amino-1-cyclohexanol 
• 931-15-7 (1R,2R)-2-aminocyclohexanol 
• 931-15-7 (1S,2S)-trans-2-aminocyclohexanol 
• 882409-01-0 (S)-mandelic acid salt of (1R,2R)-2-trans-2-(benzylamino)cyclohexanol 
• 882409-00-9 (R)-mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol 
• 121282-70-0 (1S,2S)-2-tert-Butoxycarbonylamino-1-cyclohexanol 
• 365996-28-7 (1S,2S)-2-(tert-butoxycarbonylamino)cyclohexyl methanesulfonate 
• 365996-29-8 (1R,2S)-2-(N-tert-butyloxycarbonylamino)-1-azidocyclohexane 
• 365996-30-1 tert-butyl ((1S,2R)-2-aminocyclohexyl)carbamate 
• 1370261-95-2 tert-butyl (1S,2R)-2-(4-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-5-carbamoylpyrimidin-2-ylamino)cyclohexylcarbamate 
• 1370261-98-5 4-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-2-((1R, 2S)-2-aminocyclohexylamino)pyrimidine-5-carboxamide acetic acid salt 

Relevant articles and documents

Practical resolution of racemic trans-2-benzylaminocyclohexanol with di-p-toluoyl-l-tartaric acid via diastereomeric salt formation based on the Pope and Peachey method

A new resolution process for racemic trans-2-benzylaminocyclohexanol 2, a key intermediate for chiral pharmaceuticals, was investigated. Di-p-toluoyl-l-tartaric acid 15 was found to be a new practical resolving agent in terms of stability and productivity of the resolution system. Resolution conditions were optimized based on the Pope and Peachey method, and the best result was obtained when HCl was added to the resolution system as a supplemental acid; 2/l-15/HCl = 1.0/0.6/0.4 (mol/mol/mol) (yield 92%, 99.5%de, E 92%).

Asymmetric amination of meso-epoxide with vegetable powder as a low-toxicity catalyst

This paper describes the scope and limitation of substrates subjected to asymmetric amination with epoxides catalyzed by a soluble soybean polysaccharide (Soyafibe S-DN), which we recently discovered from the reaction of 1,2-epoxycyclohexane with cyclopropylamine. Various meso-epoxides reacted with various amines afforded the corresponding products with good enantiomeric selectivity. Since it was found that pectin was found to have a catalytic ability after screening commercially available polysaccharides, we studied 33 different vegetable powders having pectic substances, and we found that many vegetable powders showed catalytic ability. These results should guide in using vegetable components as low-toxic catalysts for the production of pharmaceuticals.

Broadening the chemical scope of laccases: Selective deprotection of N-benzyl groups

Laccase from Trametes versicolor together with TEMPO has been found to be a very efficient system to deprotect N-benzylated primary amines, differing from previously described methods since it uses oxygen as a mild oxidant in aqueous medium. Chemoselective removal of the benzyl group was achieved with excellent yields when secondary amines and alcohol moieties were also present.