882409-12-3

Basic information

• Product Name: (1R,2S)-2-BenzylaMino-1-cyclohexanol
• Synonyms: (1R,2S)-2-BenzylaMino-1-cyclohexanol;(1R,2S)-2-Benzylamino-1-cyclohexanol,99%e.e.
• CAS NO: 882409-12-3
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.29606
• Mol File: 882409-12-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,2S)-2-BenzylaMino-1-cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-BenzylaMino-1-cyclohexanol(882409-12-3)
• EPA Substance Registry System: (1R,2S)-2-BenzylaMino-1-cyclohexanol(882409-12-3)

Safety Data

• Hazardous Substances Data: 882409-12-3(Hazardous Substances Data)

Usage

General Description

(1R,2S)-2-Benzylamino-1-cyclohexanol is a chemical compound that belongs to the class of amines. It consists of a cyclohexane ring with a hydroxyl group at position 1 and an amino group at position 2, which is further substituted with a benzyl group. (1R,2S)-2-BenzylaMino-1-cyclohexanol is a chiral molecule, containing two stereocenters, and its stereochemistry is described using the R/S system. It is commonly used in organic synthesis and pharmaceutical research, where its chiral nature makes it an important building block for the synthesis of various drugs and biologically active compounds.

Upstream product

• 40571-86-6 (+/-)-trans-2-(benzylamino)cyclohexanol 

Downstream Products

• 260065-86-9 (1R,2S)-2-amino-1-cyclohexanol 
• 191803-54-0 (1R,2S)-cis-2-(piperidin-1'-yl)-cyclohexanol 
• 882409-06-5 (1R,2S)-cis-2-(pyrrolidin-1'-yl)-cyclohexanol 

Relevant articles and documents

Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis

A preparatively easy and efficient protocol for the resolution of racemic 2-aminocyclohexanol derivatives is described, delivering both enantiomers with >99% enantiomeric excess (ee) by sequential use of (R)- and (S)-mandelic acid. A simple aqueous workup procedure permits the isolation of the amino alcohols in analytically pure form and the almost quantitative recovery of mandelic acid. Debenzylation of enantiopure trans-2-(N-benzyl)amino-1- cyclohexanol by hydrogenation and subsequent derivatization give access to a broad variety of diversely substituted derivatives. Furthermore, the corresponding cis isomers are readily available. Applications of these optically active aminocyclohexanols in catalyzed asymmetric phenyl transfer reactions to benzaldehydes and transfer hydrogenations of aryl ketones lead to products with up to 96% ee.