Benzyl Bromide → (S)-Methyl 1-benzyl-5-oxopyrrolidine-2-carboxylate

HRID 1029672Notes

Reaction equation

[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1.O.C(OCC)(=O)C>[CH2:13]([N:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH3:10])=[O:8])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl (2S)-5-pyrrolidone-2-carboxylate (80 g) in tetrahydrofuran (900 ml) was added sodium hydride (60% in oil, 23.5 g) by portions. After the addition, the reaction mixture was heated to 60° C., and benzyl bromide (69.8 ml) was added dropwise thereto. After 3 hours, the reaction mixture was cooled to room temperature and water (100 ml) was added dropwise thereto. The reaction mixture was poured into a mixture of ethyl acetate (2 l) and water (800 ml). The organic layer was separated, washed with brine, and dried over magnesium sulfate. Evaporation of the solvent gave an oil, which was chromatographed on silica gel (2 l) eluting with a mixture of hexane and ethyl acetate (1:1→1:2, V/V) to give methyl (2S)-1-benzyl-5-pyrrolidone-2-carboxylate (100.8 g).

Workup

additionAfter the addition
temperaturethe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customEvaporation of the solvent
customgave an oil, which
customwas chromatographed on silica gel (2 l)
washeluting with a mixture of hexane and ethyl acetate (1:1→1:2, V/V)

Sources & evidence

ORD record: ord-41ffd208cacf43a09e64464f05c3fe32
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05102877

Reaction notes

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