Triphenylphosphine → HCID 59701575, compound

Participants

Reaction Steps

To a solution of ((R)-2-azidomethyl-8-(2,6-dichloro-phenyl)-6-fluoro-2H-chromene (300 mg, 0.85 mmol) in tetrahydrofuran (10 mL) and water (0.5 mL) was added polymer-bound triphenylphosphine (˜3 mmol/g, 0.85 g, 2.6 mmol) and the reaction mixture stirred at room temperature for 43 hours. The brown suspension was then filtered through celite, the filter cake washed with ethyl acetate (50 mL) and the combined filtrates concentrated under vacuum. Chromatography with 0–10% methanol in methylene chloride plus 1% NH4OH afforded {[(2R)-8-(2,6-dichlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl}amine as a colorless oil. The oil was dissolved in ethyl acetate and made into its hydrochlorde salt (83 mg, 27%) as a white crystalline solid using excess ethereal hydrochloric acid, mp 153–155° C.; [α]D25=+220.67° (c 1% solution in MeOH); MS (ES) m/z 324.0 ([M+H]+).

Provenance & Evidence