Triphenylphosphine → HCID 69117208, compound

Participants

Reaction Steps

To a solution of (2R)-2-(azidomethyl)-7-chloro-8-o-tolylchroman (0.5 g, 1.6 mmol) in THF (15 mL) and water (0.5 mL) was added polymer-bound triphenylphosphine (3 mmol/g, 0.8 g, 2.4 mmol) and the resulting mixture was stirred at room temperature overnight. The mixture was filtered through a pad of Celite and concentrated under reduced pressure. Purification by ISCO using a solvent gradient of 0 to 10% methanol in methylene chloride provided 0.15 g of the title compound as a colorless oil. The oil was dissolved in ethyl acetate (5 mL) and to which hydrogen chloride (1.0 M in ethyl ether, 1.5 mL, 1.5 mmol) was added, solvent was removed and the solid was washed with ethyl ether (3×5 mL) to provide 0.13 g of ((2R)-7-chloro-8-o-tolylchroman-2-yl)methanamine hydrochloride as a white solid salt, mp 155° C.; MS (APPI) m/z 288 ([M+H]+); [α]D25=−55° (c=1% SOLN, MeOH).

Provenance & Evidence