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

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Reaction Conditions

Reaction Steps

To a solution of tert-butyl{(3S,5S,6R)-6-methyl-5-phenyl-2-[(4,4,4-trifluoro-2-hydroxybutyl)imino]piperidine-3-yl}carbamate (100 mg, 0.23 mmol) in acetonitrile (4.7 mL) was added pyridinium dichromate (440 mg, 1.17 mmol), and the mixture was stirred 45 min at 70° C. Pyridinium dichromate (440 mg, 1.17 mmol) was added, and the mixture was stirred 30 min 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→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (19.6 mg). MS 410.3 (M+1)

Provenance & Evidence