1,3-Dimethyl-2-imidazolidinone → tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate

HRID 1735396Notes

Reaction equation

[CH3:1]N1C(=O)N(C)CC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][C@H:27]1[CH:28]=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20].[I-].C[S+](C)C>CS(C)=O.C1COCC1>[C:19]([O:23][C:24]([N:26]1[CH2:32][CH2:31][CH2:30][C@H:27]1[CH:28]1[O:29][CH2:1]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

Conditions

Temperature: -13 °C

Procedure

DMI (350 ml) was added to a THF solution (1M, 350 ml) of sodium bis(trimethylsilyl)amide. After cooling the mixture to -13° C., a solution of N-(tert-butoxycarbonyl)-L-prolinal (57.71 g) and trimethylsulfonium iodide (73.9 g) in DMSO (350 ml) was dropwise added, and the mixture was stirred for 1 hour. The reaction mixture was poured into ice water and extracted with toluene. The extract was washed with 10% citric acid, a saturated aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to give a mixture (52.74 g) of two diastereomers of the title compound.

Workup

extractionextracted with toluene
washThe extract was washed with 10% citric acid
dry with materiala saturated aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record: ord-a237072f455a4059a0a9f6deec9a26b1
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05536737

Reaction notes

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