Water → (7-Dipropylamino-5,6,7,8-tetrahydro-naphthalen-1-yl)-methanol

Participants

Reaction Steps

Alternatively,a solution of 2-dipropylamino-8-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene (480 mg, 1.66 mMol) in tetrahydrofuran (5 mL) was added dropwise to a suspension of lithium aluminum hydride (100 mg, 2.49 mMol) in tetrahydrofuran (10 mL), and the reaction mixture was stirred at room temperature for 2.5 hours. The reaction mixture was then cooled to 0° C., and to it were added sequentially water (0.1 mL), 15% aqueous sodium hydroxide (0.1 mL) and water (0.3 mL). The suspension was then stirred at room temperature for one-half hour and was then filtered through a bed of Celite. The filtrate was concentrated in vacuo to give the title compound as a colorless, viscous oil (400 mg, 92%). The hydrochloride salt was formed and recrystallized (ethanol/diethyl ether) to give colorless crystals (m.p.=142° C.). Analysis: Calculated for C17H27NO·HCl: Theory: C, 69.02, H, 8.86, N, 4.73; Found: C, 69.03, H, 8.72, N, 4.61.

Provenance & Evidence