p-Toluenesulfonic acid → tert-butyl (S)-1-hydroxy-3-((R)-1-methyl-6-oxopiperidin-3-yl)propan-2-ylcarbamate

Participants

Reaction Steps

To a solution of (S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylate (230 mg, 0.70 mmol) in MeOH (10 mL) was added p-TSA (30 mg, 0.17 mmol) and stirred at rt overnight. TEA (1 mL) was added, followed by Boc2O (30 mg). The reaction mixture was stirred for another 30 min. The solvent was removed under vacuum to give crude product tert-butyl (S)-1-hydroxy-3-((R)-1-methyl-6-oxopiperidin-3-yl)propan-2-ylcarbamate, which was used for next step without further purification. MS ESI +ve m/z 287 (M+H).

Provenance & Evidence