882409-10-1

Basic information

• Product Name: (1S,2R)-2-BenzylaMino-1-cyclohexanol
• Synonyms: (1S,2R)-2-BenzylaMino-1-cyclohexanol;(1S,2R)-2-Benzylamino-1-cyclohexanol,99%e.e.
• CAS NO: 882409-10-1
• Molecular Formula: C₁₃H₁₉NO
• Molecular Weight: 205.29606
• Mol File: 882409-10-1.mol

Chemical Properties

• Melting Point: 51-53 °C
• Boiling Point: 339.2±35.0 °C(Predicted)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• PKA: 14.83±0.40(Predicted)
• CAS DataBase Reference: (1S,2R)-2-BenzylaMino-1-cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-2-BenzylaMino-1-cyclohexanol(882409-10-1)
• EPA Substance Registry System: (1S,2R)-2-BenzylaMino-1-cyclohexanol(882409-10-1)

Safety Data

• Hazardous Substances Data: 882409-10-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2R)-2-BenzylaMino-1-cyclohexanol is used as a building block for the synthesis of chiral drugs due to its unique stereochemistry and ability to control the stereochemical outcome of reactions. This makes it a valuable component in the development of new pharmaceuticals with specific therapeutic effects.
Used in Asymmetric Synthesis:
(1S,2R)-2-BenzylaMino-1-cyclohexanol is used as a chiral auxiliary in asymmetric synthesis to control the stereochemical outcome of a reaction. Its (1S,2R) configuration plays a key role in ensuring the desired stereochemistry is achieved, which is essential for the production of enantiomerically pure compounds.
Used in Asymmetric Catalysis:
(1S,2R)-2-BenzylaMino-1-cyclohexanol is also used as a ligand in asymmetric catalysis. Its stereochemistry aids in the selective catalysis of reactions, leading to the formation of specific enantiomers with desired biological activities. This application is particularly important in the synthesis of chiral compounds with potential pharmaceutical or agrochemical uses.

Upstream product

• 141478-34-4 1-(N-benzylamino)-2-cyclohexanone 
• 141553-09-5 (1R,2R)-trans-2-(N-benzyl)amino-1-cyclohexanol 
• 40571-86-6 (+/-)-trans-2-(benzylamino)cyclohexanol 

Relevant articles and documents

Highly enantioselective synthesis of chiral cyclic amino alcohols and conhydrine by ruthenium-catalyzed asymmetric hydrogenation

A highly efficient enantio- and diastereoselective synthesis of chiral cis-β-N-alkyl/arylamino cyclic alcohols has been realized by asymmetric hydrogenation of racemic α-amino cyclic ketones via DKR catalyzed by [RuCl2((S)-Xyl-SDP)((R,R)-DPEN)]. The enantioselectivities of the reaction were up to 99.9% ee with 99:1 cis-selectivities. A practical catalytic asymmetric synthesis of all four isomers of conhydrine was also developed.

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.

Carboxylation and Mitsunobu reaction of amines to give carbamates: Retention vs inversion of configuration is substituent-dependent

(Equation Presented) A mild method for the synthesis of carbamates from amino alcohols involves sequential carboxylation with carbon dioxide, followed by a Mitsunobu reaction. Unexpectedly, the stereochemical course of the Mitsunobu reaction is dependent on whether the carbamic acid intermediate is N-substituted with hydrogen (retention) or carbon (inversion).