HCID 22645428, compound → HCID 22645396, 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 μL) and acetone (18 mL). Osmium tetroxide (200 μL, 2.5% w/w in tert-butanol) was added, followed by sodium periodate (572 mg, 2.68 mmol) which was added portionwise. The reaction mixture was stirred at room temperature for 26 hours, then it was filtered to remove precipitate and the solvent was removed by evaporation in vacuo. The residue was partitioned between dichloromethane (25 mL) and saturated sodium chloride solution (25 mL). The organic phase was separated, dried (Na2SO4) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel (50 g) eluted with ethyl acetate:hexane:0.880 ammonia (74:25:1). The title compound was obtained as an oil (80 mg).

Provenance & Evidence