Synthesis of methyl N-Boc-(2S,4R)-4-methylpipecolate.

The Journal of organic chemistry (2010-11-26)
Kuo-Yuan Hung, Paul W R Harris, Margaret A Brimble
ABSTRACT

An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric α-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO(4)/NaIO(4) followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
L-Pipecolic acid, 99% (titration)
Sigma-Aldrich
Pipecolinic acid, 98%
Sigma-Aldrich
D-Pipecolinic acid, 99%
Sigma-Aldrich
L-Pipecolic acid, Proline homolog., 99%

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