639458-44-9

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 2-[(2S)-2-hydroxy-2-phenylethyl]-, 1,1-dimethylethyl ester, (2S)-
• CAS NO: 639458-44-9
• Molecular Formula: C18H27NO3
• Molecular Weight: 305.417
• Mol File: 639458-44-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 2-[(2S)-2-hydroxy-2-phenylethyl]-, 1,1-dimethylethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 2-[(2S)-2-hydroxy-2-phenylethyl]-, 1,1-dimethylethyl ester, (2S)-(639458-44-9)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 2-[(2S)-2-hydroxy-2-phenylethyl]-, 1,1-dimethylethyl ester, (2S)-(639458-44-9)

Safety Data

• Hazardous Substances Data: 639458-44-9(Hazardous Substances Data)

Upstream product

• 639458-43-8 (S)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 639458-46-1 (R)-2-(2-oxo-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 118811-03-3 tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylate 
• 199942-74-0 (S)-2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 250249-85-5 (R)-2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 639458-49-4 (S)-2-(2-acetoxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 639458-48-3 (R)-2-(2-acetoxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 138371-97-8 (1SR,2SR) N-tert-butoxycarbonyl-2-(β-hydroxy-β-phenylethyl)piperidine 
• 100-58-3 phenylmagnesium bromide 
• 123-62-6 propionic acid anhydride 

Downstream Products

• 497-88-1 (-)-sedamine 
• 67008-23-5 (2R)-2-((2R)-2-hydroxy-2-phenylethyl)-1-methylpiperidine 

Relevant articles and documents

Kinetic resolution of secondary alcohols using amidine-based catalysts

Kinetic resolution of racemic alcohols has been traditionally achieved via enzymatic enantioselective esterification and ester hydrolysis. However, there has long been considerable interest in devising nonenzymatic alternative methods for this transformation. Amidine-based catalysts (ABCs), a new class of enantioselective acyl transfer catalysts developed in our group, have demonstrated, inter alia, high efficacy in the kinetic resolution of benzylic, allylic, and propargylic secondary alcohols and 2-substituted cycloalkanols, and thus provide a viable alternative to enzymes.

Enantioselective Synthesis of (+)-α-Conhydrine and (-)-Sedamine by L-ProlineCatalysed α-Aminooxylation

An efficient organocatalytic approach to the enantioslective synthesis of two important piperidine alkaloids, namely (+)α-conhydrine (98% ee) and (-)-sedamine (95 % ee), by L-pro-line-catalysed α-aminooxylation of aldehydes has been developed. The strategy involves an intramolecular cyclization to construct the piperidine core.

Remote Stereocenter Discrimination in the Enzymatic Resolution of Piperidine-2-ethanol. Short Enantioselective Synthesis of Sedamine and Allosedamine

Kinetic resolution of N-Boc-piperidine-2-ethanol (2), a case of remote stereocenter discrimination, was accomplished by sequential transesterification mediated by two enzymes, Lipase PS and porcine pancreatic lipase, showing opposite enantioselectivity. The gram-scale availability of the two enantiomeric N-Boc alcohols 2a (R) and 2c (S) enlarges their synthetic exploitation for the enantioselective preparation of piperidine alkaloids. As an example, the convenient three-step synthesis of both the enantiomers of sedamine and allosedamine is described.