HCID 10946429, compound → HCID 11077426, compound

Participants

Reaction Steps

A 500 ml autoclave was charged in a glove box with 2 g (6.73 mmol) of (Z)-2-acetyl-1,2,3,4,5,6,7,8-octahydro-1-(p-methoxybenzylidene)isoquinoline (prepared according to any one of Examples 1-4), 170 ml of methanol and 1.3 mg (0.0017 mmol; S/Ru =4000) of Ru(CH3COO)2 (BIPHEMP) as the catalyst. The hydrogenation was carried out at 100° C. and 35 bar for 24 hours. The hydrogenation solution was evaporated and the residue was dissolved in diethyl ether. After separation of the catalyst over silica gel and evaporation of the filtrate, there were obtained 1.98 g of (S)-2-acetyl-1 -(p-methoxybenzyl) -1,2,3,4,5,6,7,8-octahydroisoquinoline of 98.3% e.e., which was recrystallized from diisopropyl ether. [α]D20 =+53° (c=1 in CH3OH); 100% e.e., m.p. 80°-81.5° C.

Provenance & Evidence