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

Description

(1R,2S)-2-BenzylaMino-1-cyclohexanol is a chiral amine compound characterized by a cyclohexane ring with a hydroxyl group at position 1 and an amino group at position 2, which is substituted with a benzyl group. Its stereochemistry is defined by the R/S system, with the specific configuration being 1R,2S. (1R,2S)-2-BenzylaMino-1-cyclohexanol is utilized in various fields due to its unique structural and stereochemical features.

Uses

Used in Organic Synthesis:
(1R,2S)-2-BenzylaMino-1-cyclohexanol serves as a crucial building block in organic synthesis, where its distinct structure and chirality are exploited to construct complex organic molecules. Its utility in this field is attributed to its ability to form a wide range of derivatives, making it a versatile component in the synthesis of various compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (1R,2S)-2-BenzylaMino-1-cyclohexanol is used as a key intermediate in the development of drugs and biologically active compounds. Its chiral nature allows for the creation of enantiomerically pure substances, which is essential for ensuring the desired biological activity and minimizing potential side effects. (1R,2S)-2-BenzylaMino-1-cyclohexanol's unique structure also enables it to be a part of novel drug candidates with specific targeting and therapeutic properties.
Used in Chiral Chemical Development:
(1R,2S)-2-BenzylaMino-1-cyclohexanol is also utilized in the development of chiral chemicals, which are essential in various chemical and industrial processes. (1R,2S)-2-BenzylaMino-1-cyclohexanol's defined stereochemistry makes it a valuable reference for the synthesis of other chiral molecules and in the study of stereoselective reactions.

Upstream product

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

Downstream Products

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