Triacetoxyperiodinane → 1,1-Dimethylethyl (2S)-4,4-difluoro-2-formyl-1-pyrrolidinecarboxylate
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([N:30]1[CH2:34][C:33]([F:36])([F:35])[CH2:32][C@H:31]1[CH2:37][OH:38])=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28]([N:30]1[CH2:34][C:33]([F:35])([F:36])[CH2:32][C@H:31]1[CH:37]=[O:38])=[O:29])([CH3:26])([CH3:25])[CH3:24]Participants
4
Procedure
Dess Martin Periodinane (0.9 g, 0.0021 mol) was added in one portion to a solution of (S)-4,4-difluoro-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.4 g, 0.0016 mol) in DCM (50 mL) under an inert atmosphere. The reaction was stirred until completion (about 2 h) and then quenched with saturated solution of sodium thiosulphate, extracted with DCM (3×100 mL) washed with brine (50 mL), dried over anhydrous sodium sulphate, and concentrated using a rotary evaporator to afford 0.35 g of the desired (S)-4,4-difluoro-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown colored oil product.