3-(Triphenyl-lambda~5~-phosphanylidene)butan-2-one → (2S)-5-allyloxycarbonylimino-1-methyl-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine

HRID 1650298Notes

Reaction equation

[CH2:1]([O:4][C:5]([N:7]=[C:8]1[N:12]([CH3:13])[C@H:11]([CH:14]=O)[CH2:10][CH2:9]1)=[O:6])[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:23]([CH3:27])[C:24](=[O:26])[CH3:25])C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]([N:7]=[C:8]1[N:12]([CH3:13])[C@H:11]([CH:14]=[C:23]([CH3:27])[C:24](=[O:26])[CH3:25])[CH2:10][CH2:9]1)=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (2S)-5-allyloxycarbonylimino-2-formyl-1-methylpyrrolidine (0.46 g) in toluene (20 ml) was added 3-triphenylphosphoranylidenebutan-2-one and the mixture was stirred at 80° C. for 2 hours. The solvent was evaporated and the residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:2 V/V) to give (2S)-5-allyloxycarbonylimino-1-methyl-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (0.54 g).

Workup

customThe solvent was evaporated
customthe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (1:2 V/V)

Sources & evidence

ORD record: ord-d1bb2e3e8816403e87b1e6dbab9cba68
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04923857

Reaction notes

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