212556-96-2

Upstream product

• 1530-32-1 ethyltriphenylphosphonium bromide 
• 212556-95-1 (S)-N-(benzyloxycarbonyl)-2-formylpiperidine 
• 501-53-1 benzyl chloroformate 
• 3433-37-2 piperidin-2-ylmethanol 
• 212557-00-1 (S)-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester 
• 105706-75-0 1-benzyloxycarbonyl-2-hydroxymethylpiperidine 

Downstream Products

• 251995-64-9 (-)-benzyl (S)-2-[(S)-2-hydroxypropyl]piperidine-1-carboxylate 
• 251995-67-2 (-)-benzyl (S)-2-[(R)-2-hydroxypropyl]piperidine-1-carboxylate 

Relevant academic research and scientific papers

Protecting-Group-Directed Regio- and Stereoselective Oxymercuration-Demercuration: Synthesis of Piperidine Alkaloids Containing 1,2- and 1,3-Amino Alcohol Units

An efficient synthesis of naturally occurring 1,2- and 1,3-amino alcohol unit containing 2-substituted piperidine alkaloids and their analogues has been developed from l -pipecolinic acid. The protocol describes the regio- and stereoselective oxymercuration-demercuration of 2-alkenyl piperidines based on protecting groups to give piperidine alkaloids as a key step.

Short syntheses of (S)-pipecolic acid, (R)-coniine, and (S)-δ-coniceine using biocatalytically-generated chiral building blocks

The kinetic resolutions of both (±)-N-(benzyloxycarbonyl-2- (hydroxymethyl)piperidine [(±)-5] and (±)-N(tert-butoxycarbonyl)-2- (hydroxymethyl)piperidine [(±)-6] catalyzed by the enzyme acylase I from Aspergillus species (AA-I) afforded the chiral building blocks (S)-5 and (S)- 6, respectively; which were used for the syntheses of the title natural products and derivatives of (S)-pipecolic acid. The syntheses were short (2- 4 steps) and proceeded with satisfactory overall yield.