Ammonia → (4S)-2-(1-aminoethyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol

Participants

Reaction Steps

To a solution of (S,E)-4-(3,4-dichlorophenyl)-2-ethylidene-3,4-dihydronaphthalen-1(2H)-one (42) (0.60 g, 1.89 mmol) in THF (8 mL) at ambient temperature was added ammonia solution (2.0 M in MeOH, 2.83 mL, 5.67 mmol). The reaction mixture was stirred for 4 h before NaBH4 (0.14 g, 3.78 mmol) was added. The reaction mixture was stirred for 2 h before being quenched by a saturated solution of NH4Cl (8 mL). The product was extracted with diethyl ether (30 mL×2), dried and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane/0.1% DEA=1:7 to 1:5) to give (4S)-2-(1-aminoethyl)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-ol (43) (0.50 g, 50%).

Provenance & Evidence