154002-73-0

Basic information

• Product Name: (+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID
• Synonyms: 4-METHYL-PIPERIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;2-AMino-terephthalic acid 1-tert-butyl ester 4-Methyl ester;(2R,4R)-N-Boc-4-methyl-pipecolinic acid
• CAS NO: 154002-73-0
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.3
• Mol File: 154002-73-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID(154002-73-0)
• EPA Substance Registry System: (+/-)-TRANS-N-BOC-4-METHYL-PIPECOLINIC ACID(154002-73-0)

Safety Data

• Hazardous Substances Data: 154002-73-0(Hazardous Substances Data)

Upstream product

• 173369-02-3 (N-(tert-butoxycarbonyl)-(2R,4R)-4-methylpiperidine-2-yl)methanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 954378-99-5 ((2S,3S)-3-(2-methylallyl)oxiran-2-yl)methanol 
• 954379-07-8 (N-(tert-butoxycarbonyl)-(6R)-1,2,3,6-tetrahydro-4-methylpyridine-2-yl)methanol 
• 954379-06-7 (2R)-N-allyl-N-(tert-butoxycarbonyl)-2-amino-4-methyl-4-penten-1-ol 

Downstream Products

• 74892-81-2 (2R-trans)-4-Methyl-2-piperidinecarboxylic acid 

Relevant articles and documents

Enantioselective synthesis of trans-4-methylpipecolic acid

(Chemical Equation Presented) An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described. It is based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring. The stereogenic center at C-4 is set by stereoselective hydrogenation that is directed by the alcohol functionality of an intermediate and proceeds with good diastereomeric control (trans/cis 16/1). Crystallization of the Boc-protected amino acid afforded the target products with excellent chemical (98% de) and enantiomeric purity (99% ee).