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  • An efficient synthesis of enantiomerically pure (R)-pipecolic acid, (S)-proline, and their N-alkylated derivatives.

An efficient synthesis of enantiomerically pure (R)-pipecolic acid, (S)-proline, and their N-alkylated derivatives.

The Journal of organic chemistry (2007-01-30)
Antoine Fadel, Nabil Lahrache
PMID17256910
ABSTRACT

Enantiomerically pure (R)-(+)-pipecolic acid was synthesized in four steps and 42% overall yield starting from dihydropyran and (R)-alpha-methylbenzylamine. A general short strategy is also described for preparing (S)-proline (47.5% overall yield) and derivatives.

MATERIALS
Product Number
Brand
Product Description
115568
Sigma-Aldrich
(S)-(−)-α-Methylbenzylamine, 98%
77879
Supelco
(R)-(+)-α-Methylbenzylamine, for chiral derivatization, LiChropur™, ≥99.0%
M31104
Sigma-Aldrich
α-Methylbenzylamine, 99%
726621
Sigma-Aldrich
(R)-(+)-α-Methylbenzylamine, ChiPros®, produced by BASF, ≥99.0%
77880
Sigma-Aldrich
(R)-(+)-α-Methylbenzylamine, purum, ≥98.0% (sum of enantiomers, GC)
115541
Sigma-Aldrich
(R)-(+)-α-Methylbenzylamine, 98%