Sodium Methoxide → (S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylate

Participants

Reaction Steps

To a solution of (S)-tert-butyl 4-((R)-5-tert-butoxy-2-((methylamino)methyl)-5-oxopentyl)-2,2-dimethyloxazolidine-3-carboxylate (212 mg, 0.53 mmol) in absolute MeOH was added a NaOMe solution in MeOH (33%, 0.4 mL). The resulting solution was stirred for 24 h. The solvent was removed under reduced pressure, the residue was dissolved in EtOAc (50 mL), washed with 1 M HCl, sat. aq. NaHCO3, brine, and dried over Na2SO4, filtered and evaporated to give (S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylate (160 mg, 92%). MS ESI +ve m/z 564 (M+Na).

Provenance & Evidence