140695-98-3

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 3-[(1-oxobutoxy)methyl]-, 1,1-dimethylethyl ester, (R)-
• CAS NO: 140695-98-3
• Molecular Formula: C15H27NO4
• Molecular Weight: 285.384
• Mol File: 140695-98-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 3-[(1-oxobutoxy)methyl]-, 1,1-dimethylethyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 3-[(1-oxobutoxy)methyl]-, 1,1-dimethylethyl ester, (R)-(140695-98-3)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 3-[(1-oxobutoxy)methyl]-, 1,1-dimethylethyl ester, (R)-(140695-98-3)

Safety Data

• Hazardous Substances Data: 140695-98-3(Hazardous Substances Data)

Upstream product

• 140645-20-1 t-butyl (R,S)-3-<(butyryloxy)methyl>-1-piperidine-carboxylate 

Downstream Products

• 116574-71-1 tert-butyl (3R)-3-(hydroxymethyl)piperidine-1-carboxylate 

Relevant articles and documents

Chemical and enzymatic resolution of (R,S)-N-(tert-Butoxycarbonyl)-3-hydroxymethylpiperidine

(S)-N-(tert-Butoxycarbonyl)-3-hydroxymethylpiperidine 1 was made from (R,S)-3-hydroxymethylpiperidine 2 via fractional crystallization of the corresponding L(-)-dibenzoyl tartarate salt 3 followed by hydrolysis and acylation. Lipase from Pseudomonas cepacia was found to be the best enzyme for the stereospecific resolution of (R,S)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 4. (S)-N-(tert-Butoxycarbonyl)-3-hydroxymethylpiperidine 1 was obtained in 16% yield and >95% enantiomeric excess (ee) by hydrolysis of (R,S)-acetate 5 by lipase PS from Pseudomonas cepacia. Lipase PS-catalyzed esterification of the (R,S)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 4 with succinic anhydride provided the S-hemisuccinate ester 6, which could be easily separated and hydrolyzed by base to the (S)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 1. The yield and ee could be improved greatly by repetition of the process. Using the repeated esterification procedure (S)-N-(tert-butoxycarbonyl)-3-hydroxymethylpiperidine 1 was obtained in 32% yield (maximum theoretical yield 50%) and 98.9% ee.