tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate → tert-butyl (2S)-2-benzoylpyrrolidine-1-carboxylate
Reaction equation
[C:1]1([Mg]Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]([N:16]1[CH2:22][CH2:21][CH2:20][C@H:17]1[CH:18]=[O:19])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>>[C:9]([N:16]1[CH2:22][CH2:21][CH2:20][C@H:17]1[C:18](=[O:19])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]Participants
3
Procedure
10 ml (20 mmol) 2 M phenylmagnesium chloride (tetrahydrofuran) and 1.99 g (10 mmol) BOC-L-prolinal were allowed to react at −60–40° C. for 60 min according to procedure F. Yield of the crude product 3.06 g. The product was purified with a silica column using 16% ethyl acetate in petroleum ether as eluent. Yield 2.18 g (7.6 mmol, 76%). The product was oxidized to the corresponding ketone according to procedure G. Yield of crude product 3.15 g. The product was purified with a silica column using 20–25% ethyl acetate in petroleum ether as eluent. Yield 1.65 g (6.0 mmol, 79%).
Workup
- customto react at −60–40° C. for 60 min