Ethyl Acetate → HCID 71227140, compound

Participants

Reaction Steps

To a colorless solution of 1-[(3-{[4-(methyloxy)phenyl]methyl}-2-oxo-7-{[(phenylmethyl)oxy]methyl}-1-oxa-3-azaspiro[4.5]dec-7-yl)methyl]-1H-benzimidazole-6-carbonitrile (1.55 g, 2.81 mmol) in acetonitrile (28.1 mL) was added ceric ammonium nitrate (3.09 g, 5.63 mmol) and the mixture was stirred at room temperature. The reaction was then heated to 60° C. and stirred for 22 h. The reaction was then cooled to RT and the orange suspension was filtered using Buchner vacuum filtration. The solid was rinsed with MeCN (3×20 mL) and the filtrate concentrated to yield a glassy orange oil. Ethyl acetate (75 mL) and 2 N NaOH (50 mL) were then added. The mixture was filtered using Buchner vacuum filtration. The filtrate layers were separated and the aqueous layer was washed with EtOAc (50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The concentrated organic layer was loaded onto florisil and purified using silica gel chromatography CISCO): 1-4% methanol/dichloromethane (25 min), 40 g silica. The product eluted at 11 minutes to yield 1-[(2-oxo-7-{[(phenylmethyl)oxy]methyl}-1-oxa-3-azaspiro[4.5]dec-7-yl)methyl]-1H-benzimidazole-6-carbonitrile as a orange foam (653 mg, 51% yield). MS (m/z) 431.0 (M+H+).

Provenance & Evidence