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

HRID 13776Notes

Reaction equation

HRID 13776 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

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 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.

Workup

  1. distillationwas mostly distilled off under reduced pressure
  2. extractionfollowed by extraction with ethyl acetate twice

Sources & evidence

ORD record
ord-86806af5067741a78f043db6e42cb4c4
Source dataset
uspto-grants-2010_06
Patent number
US07728131B2

Reaction notes

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