882409-00-9

Basic information

• Product Name: (R)-mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol
• Synonyms: (R)-mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol
• CAS NO: 882409-00-9
• Molecular Weight: 357.45
• Mol File: 882409-00-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol(882409-00-9)
• EPA Substance Registry System: (R)-mandelic acid salt of (1S,2S)-2-trans-2-(benzylamino)cyclohexanol(882409-00-9)

Safety Data

• Hazardous Substances Data: 882409-00-9(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 286-20-4 cyclohexane-1,2-epoxide 
• 611-71-2 (R)-Mandelic Acid 
• 40571-86-6 rac-(1R,2R)-2-(benzylamino)cyclohexanol 

Downstream Products

• 611-71-2 (R)-Mandelic Acid 
• 322407-34-1 (1S,2S)-trans-2-(N-benzyl)amino-1-cyclohexanol 
• 931-15-7 (1S,2S)-trans-2-aminocyclohexanol 

Relevant articles and documents

An improved and efficient process for the scalable preparation of optically pure trans-2-aminocyclohexanols

An improved and efficient process has been developed for a green and scalable preparation of optically pure (1R,2R) - and (1S,2S) -trans-2-aminocyclohexanols. The process utilised hot water to promote the aminolysis of cyclohexene oxide by benzylamine to afford racemic trans-2-(benzylamino)cyclohexanols, which were resolved by sequential and repeated use of (R)- and (S)-mandelic acid. Finally, after treatment of the two salts sequentially with HCl and NaOH and recovery of mandelic acid, liberation was achieved of the optically pure trans-2-benzylaminoaminocyclohexanols which were smoothly debenzylated using a low loading of a Pd/C catalyst to the trans-2-aminocyclohexanols. The synthetic route has been successfully applied to large-scale (1 mol) preparations in good yield.