Triphenylphosphine → HCID 24878193, compound

Participants

Reaction Steps

To a solution of (R)-2-(azidomethyl)-8-(2,6-dichlorophenyl)-6-fluorochroman (0.26 g, 0.73 mmol) in tetrahydrofuran (10 mL) and water (1 mL) was added polymer-bound triphenylphosphine (˜3 mmol/g, 0.74 g, 2.2 mmol) and the reaction mixture stirred at room temperature for 2 days. The brown suspension was then filtered through celite, the filter cake washed with ethyl acetate (50 mL) and the combined filtrates concentrated under vacuum. The solvent was removed under vacuum. Chromatography with 0–10% methanol in methylene chloride plus 1% NH4OH afforded {[(R)-8-(2,6-dichlorophenyl)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]methyl}amine as a colorless oil. The colorless oil was dissolved in ethyl acetate and made into its hydrochloride salt (0.18 g, 67%) as a white crystalline solid using excess ethereal hydrochloric acid, mp 190–192° C.; MS (ES) m/z 326.0 ([M+H]+); [α]D25=−4.39° (c 1% solution in MeOH).

Provenance & Evidence