Hydrochloric Acid → Ammonia

Participants

Reaction Steps

2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethanol (Prepared according to WO9843942, 390 mg, 0.88 mmol) was dissolved in tetrahydrofuran (6 ml), triphenylphosphine (344 mg, 1.31 mmol) then di-tert-butyl(E)-diazene-1,2-dicarboxylate (265 mg, 1.31 mmol) was added and the mixture was stirred for 20 minutes. tert-butyl[2-(4-hydroxyphenyl)ethyl]carbamate (Prepared according to WO2004/020415, 311 mg, 1.31 mmol) was then added and the reaction was stirred over night. Hydrogen chloride (4M in diethyl ether, ml) was added and left to stir for 3 days, then hydrochloric acid (2M, 5 ml) was added and after 1 hour the mixture was washed with diethyl ether, basified with 2N sodium hydroxide, extracte with diethyl ether, dried (magnesium sulphate), filtered and the solvents removed in vacuo and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (242/8/0.8 to 95/5/0.5 by volume) to furnish the title compound as a colourless oil, 100 mg.

Provenance & Evidence