(S)-tert-Butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate → tert-Butyl ((S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl-2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate (9 g, 30.1 mmol) was dissolved in 80% CH3CO2H (90 ml). The solution was stirred at 50° C. during 1.5 hr and evaporated to dryness at reduced pressure. The residue was dissolved in Et2O (150 ml) and washed with saturated NaHCO3 (4×100 mL). The organic layer was dried over Na2SO4, filtered, and the solvent removed under reduced pressure to give tert-butyl (S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate (6.2 g, 79.5%) as an oil, which was used in the next step without further purification.

Provenance & Evidence