Hydrochloric Acid → 3-(4-Tert-butoxycarbonylaminophenyl)propanol

Participants

Reaction Conditions

Reaction Steps

Diisobutylaluminium hydride(l.5 M in toluene, 30.5 ml, 45.8 mmol) was added dropwise to a stirred solution of ethyl 3-(4-tert-butoxycarbonylaminophenyl)propionate (6.10 g, 20.8 mmol) in tetrahydrofuran (60 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hour. 2N-hydrochloric acid was added to the mixture and the mixture was extracted with ethyl acetate. The extract was successively washed with water, saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:2) to give 3-(4-tert-butoxycarbonylaminophenyl)propanol as a colorless oil (2.66 g, 51%).

Provenance & Evidence