(3S)-tert-butyl 3-((6S)-6-((2-methyloxiran-2-yl)methyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate → (S)-tert-butyl 3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate

Participants

Reaction Steps

A solution of (3S)-tert-butyl 3-((6S)-6-((2-methyloxiran-2-yl)methyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate (2.87 g, 6.67 mmol) in dry THF (50 mL) was cooled to 0° C. After 20 min, the mixture was allowed to warm up to rt slowly. The mixture was stirred 2 h at rt, before being cooled to 0° C. again. The mixture was quenched with water (10 mL), 1% aq HCl (25 mL), diluted with EtOAc (120 mL). After separation, the organic layer was washed with brine (20 mL), dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 120 g silica gel column, eluted with a 50-100% EtOAc in hexanes gradient, to afford (S)-tert-butyl 3-((S)-6-(2-hydroxy-2-methylpropyl)-2-oxo-6-phenyl-1,3-oxazinan-3-yl)piperidine-1-carboxylate (0.55 g, 19% yield). LC-MS Method 1 tR=1.64 min., m/z 455 (M+Na).

Provenance & Evidence