Water → HCID 22645419, compound

Participants

Reaction Steps

1-Hexyl-3,4-dimethyl-4-(3-vinylphenyl)piperidine (Example 26, 200 mg, 0.67 mmol) was dissolved in a mixture of water (2 mL) and acetone (18 mL). 4-methylmorpholine N-oxide (172 mg, 1.47 mmol) was added with stirring followed by osmium tetroxide (200 μL, 2.5% w/w in tert-butanol). The reaction mixture was stirred at room temperature for 4 hours before the solvent was removed by evaporation in vacuo. The residue was partitioned between dichloromethane (25 mL) and water (25 mL). The organic phase was separated and dried (Na2SO4). Concentration in vacuo gave a residue which was purified by column chromatography on silica gel (10 g) eluted with a gradient of ethyl acetate:hexane:ammonium hydroxide solution (50:49:1 to 60:33:1), followed by ethyl acetate:methanol:ammonium hydroxide solution (94:5:1). Combination of the appropriate fractions and evaporation to dryness in vacuo gave the product as a yellow oil (145 mg).

Provenance & Evidence