Acetic Acid → tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

HRID 1029633Notes

Reaction equation

C([O:9][C@H:10]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]1)(=O)C1C=CC=CC=1.C[O-].[Na+].C(O)(=O)C>CO>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][C@H:10]([OH:9])[CH2:11]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-3-benzoyloxy-1-t-butoxycarbonylpyrrolidine (21 g) in methanol (210 ml) was added 28% sodium methoxide in methanol solution (18 ml) under nitrogen at -10° C. After stirring at 0° C. for 2 hours, acetic acid (4.95 ml) was added thereto and the mixture was evaporated. The residue was extracted with ethyl acetate and the extract was washed with water and brine successively. The dried organic solvent was evaporated to give (S)-1-t-butoxycarbonyl-3-hydroxypyrrolidine (19.0 g).

Workup

customthe mixture was evaporated
extractionThe residue was extracted with ethyl acetate
washthe extract was washed with water and brine successively
customThe dried organic solvent was evaporated

Sources & evidence

ORD record: ord-1c566495dbd24246989169494f12ab63
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102877

Reaction notes

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