Acetic Acid → O1-tert-butyl O3-methyl 4-hydroxy-3-methyl-piperidine-1,3-dicarboxylate

Participants

Reaction Steps

To an ice-cold solution of O1-tert-butyl O3-methyl 3-methyl-4-oxo-piperidine-1,3-dicarboxylate (0.5 g, 1.85 mmol) in MeOH (10 mL) was added acetic acid (0.5 mL) followed by portion wise addition of sodium cyanoborohydride (0.12 g, 1.85 mmol). The mixture was stirred at rt for 4 h. After completion of reaction (by TLC), water (50 mL) was added and extracted with DCM (3×100 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain the product as a viscous liquid (0.5 g). MS: 274.13 [M+H]+.

Provenance & Evidence