Tetrabutylammonium Fluoride → (5S)-5-(Hydroxymethyl)-1-methyl-2-pyrrolidinone
Reaction equation
[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][C@H:28]1[N:32]([CH3:33])[C:31](=[O:34])[CH2:30][CH2:29]1)(C(C)(C)C)(C)C>C1COCC1>[OH:26][CH2:27][C@H:28]1[N:32]([CH3:33])[C:31](=[O:34])[CH2:30][CH2:29]1Participants
4
Procedure
Bu4NF (1 mol THF solution, 17.5 ml, 17.5 mmols) was added to a THF (100 ml) solution of the (5S)-5-[(tert-butyldimethylsilyloxy)methyl]-1-methylpyrrolidin-2-one (3.84 g, 15.8 mmols), and the mixture was stirred for 15 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and then the residue was subjected to silica gel column chromatography (SiO2 150 g, MeOH—CHCl3 1:9 v/v) to obtain (5S)-5-(hydroxymethyl)-1-methylpyrrolidin-2-one as a mixture (2.46 g) with inseparable impurities.