Methanol → [(R)-6-fluoro-8-(2-methoxyphenyl)-3,4-dihydro-2H-chromen-2-yl]methanamine

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To a solution of (R)-2-(azidomethyl)-6-fluoro-8-(2-methoxyphenyl)-chroman (210 mg, 0.67 mmol) in tetrahydrofuran (15 mL) and water (0.5 mL) was added triphenylphosphine (0.21 g, 0.80 mmol) and the reaction mixture stirred at room temperature for 24 hours. Chromatography with 0–10% methanol in ethyl methylene chloride plus 1% NH4OH afforded [(R)-6-fluoro-8-(2-methoxyphenyl)-3,4-dihydro-2H-chromen-2-yl]methanamine as a colorless oil. The oil was dissolved in ethyl acetate and made into its hydrochloride salt (0.95 g, 69%) as a white solid using excess ethereal hydrochloric acid, mp 100° C. decomposed; MS (ES) m/z 288.1 ([M+H]+); [α]D25=−34.64° (c=5.7 mg/0.7 mL MeOH).

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