Triphenylphosphine → 4-Butyl-1-phenylpyrrolidin-2-one
Reaction equation
[C:1]1([NH:7][C:8](=[O:17])[CH2:9][CH:10]([CH2:15]O)[CH2:11][CH2:12][CH2:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:11]([CH:10]1[CH2:15][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8](=[O:17])[CH2:9]1)[CH2:12][CH2:13][CH3:14]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-hydroxymethylheptanoic acid phenylamide (0.61 g, 2.6 mmol) in THF (30 mL) under argon was added triphenylphosphine (1.36 g, 5.2 mmol). The solution was cooled to 0° C. and diethyl azodicarboxylate (0.61 mL, 3.9 mmol) was added dropwise. The reaction mixture was warmed up to rt and stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with dichloromethane (3×50 mL). The combined extractions were dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 1:2) to afford 4-butyl-1-phenylpyrrolidin-2-one as a white solid (0.4 g, 72%). MS(ES) m/e 218 [M+H]+.
Workup
- temperatureThe reaction mixture was warmed up to rt
- customThe reaction was quenched with saturated aqueous NaHCO3 (50 mL)
- extractionextracted with dichloromethane (3×50 mL)
- extractionThe combined extractions
- dry with materialwere dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 1:2)
Sources & evidence
- ORD record
- ord-8d43c8feb4254c3b9264d070f66bb0fa
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07456211B2
Reaction notes
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