Sodium hydride → tert-butyl (2S)-2-(oxiran-2-yl)pyrrolidine-1-carboxylate
Reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[C:8]([O:12][C:13]([N:15]1[CH2:21][CH2:20][CH2:19][C@H:16]1[CH:17]=[O:18])=[O:14])([CH3:11])([CH3:10])[CH3:9]>CS(C)=O.C1COCC1>[C:8]([O:12][C:13]([N:15]1[CH2:21][CH2:20][CH2:19][C@H:16]1[CH:17]1[O:18][CH2:4]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
DMSO (200 ml) was added to sodium hydride (60% NaH, 24.0 g), and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was cooled to room temperature and THF (200 ml) was added. The mixture was cooled to -5° C., and thereto was dropwise added a solution of trimethylsulfonium iodide (122.5 g) in DMSO (400 ml). After stirring for 1 minute, a solution of N-(tert-butoxycarbonyl)-L-prolinal (60.0 g) in THF (200 ml) was added quickly, followed by stirring at 0° C. for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give the crude product of the title compound (54.9 g), which was then used in the next reaction without purification.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- temperatureThe mixture was cooled to -5° C.
- stirringAfter stirring for 1 minute
- stirringby stirring at 0° C. for 1 hour
- extractionextracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a6ffd73171e14deca109980b888f43e2
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05506256
Reaction notes
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