Sodium Bicarbonate → HCID 57284591, compound

Participants

Reaction Steps

To a solution of 8-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocycloheptene-2-carboxamide (3.00 g) in dry tetrahydrofuran (90 ml) was gradually added lithium aluminum hydride (1.02 g) under ice-cooling and nitrogen atmosphere. The mixture was then heated to reflux for 3 hours. Saturated sodium bicarbonate solution was added dropwise to the reaction mixture under ice-cooling, and the resulting precipitate was filtered off and washed with ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (30:1 to 5:1) to afford (2S)-1-[N-(3-aminomethyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-benzylamino]-3-phenoxy-2-propanol (2.75 g).

Provenance & Evidence