Water → tert-Butyl[(5R,6S,8S)-3-(2-methoxypropan-2-yl)-5-methyl-6-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-yl]carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl{(3S,5S,6R)-2-[(2-hydroxy-3-methoxy-3-methylbutyl)imino]-6-methyl-5-phenylpiperidin-3-yl}carbamate (196 mg, 0.47 mmol) in acetonitrile (4.7 mL) was added pyridinium dichromate (880 mg, 2.34 mmol), and the mixture was stirred 1 h at 70° C. The mixture was cooled to ambient temperature and saturated aqueous sodium bicarbonate was added. Water was added, and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase chromatography (C-18, 95% water/acetonitrile→15% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (36 mg). MS 400.4 (M+1).

Provenance & Evidence