Triacetoxyperiodinane → Tert-butyl 2-formyl-2-methylpyrrolidine-1-carboxylate
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][CH2:33][CH2:32][C:31]1([CH2:36][OH:37])[CH3:35])=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1([CH:36]=[O:37])[CH3:35])=[O:29])([CH3:26])([CH3:25])[CH3:24]Participants
4
Procedure
Dess Martin Periodinane (7.8 g, 0.0186 mol) was added in one portion to the solution of (rac)-2-hydroxymethyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (2 g, 0.0093 mol) in DCM (50 mL) under an inert atmosphere. The reaction was stirred until completion (about 2 h) 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 1.6 g (84%) of (rac)-2-formyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown colored oil.