Methanol → (3S,4S)-3-(Dimethylamino)-4-hydroxy-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][CH3:14])[C@@H:10]([OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:18]O>>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@H:10]([OH:15])[C@@H:11]([N:13]([CH3:18])[CH3:14])[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 46834660(3S,4S)-tert-Butyl 3-hydroxy-4-(methylamino)pyrrolidine-1-carboxylate

Product 1

HCID 66674043(3S,4S)-3-(Dimethylamino)-4-hydroxy-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester

Procedure

This compound was prepared in the same manner as in Reference Example 25 (step 1), except that (3S,4S)-1-(t-butoxycarbonyl)-3-hydroxy-4-(methylamino)pyrrolidine (Tetrahedron: Asymmetry, 2001, 12, 2989-2997) was used, and that the reaction was conducted for 1 hour under ice cooling, the reaction solution was alkalified with a 1N aqueous sodium hydroxide solution and methanol was mostly distilled off under reduced pressure, followed by extraction with ethyl acetate twice.