A convenient formal synthesis of (2S,3S)-3-hydroxy pipecolic acid

A convenient synthesis of (2S,3S)-3-hydroxy pipecolic acid starting from inexpensive and easily available l-(+)-tartaric acid has been described.

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(S)-5-((S)-1,2-Dihydroxyethyl)furan-2(5H)-oneC6H8O4[α]D25=+39 (c 1.0, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (5S,1aS)

(S)-5-((S)-1,2-Dihydroxyethyl)dihydrofuran-2(3H)-oneC6H10O4[α]D25=+32 (c 1.0, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (5S,1aS)

(S)-5-((R)-1-Azido-2-((tert-butyldimethylsilyl)oxy)ethyl)dihydrofuran-2(3H)-oneC12H23N3O3Si[α]D25=-8 (c 1.0, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (5S,1aR)

(S)-5-((R)-1-Amino-2-((tert-butyldimethylsilyl)oxy)ethyl)dihydrofuran-2(3H)-oneC12H25NO3Si[α]D25=+22 (c 1.0, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (5S,1aR)

(5S,6R)-6-(((tert-Butyldimethylsilyl)oxy)methyl)-5-hydroxypiperidin-2-oneC12H25NO3Si[α]D25=+21 (c 1.0, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (5S,6R)

(2R,3S)-tert-Butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-3-hydroxypiperidine-1-carboxylateC17H35NO4Si[α]D25=-39.19 (c 1.0, CHCl3)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (2R,3S)

(2R,3S)-tert-Butyl 3-hydroxy-2-(hydroxymethyl)piperidine-1-carboxylateC11H21NO4Ee ∼99%[α]D25=-27 (c 1.0, MeOH)Source of chirality: l-(+)-tartaric acidAbsolute configuration: (2R,3S)