HCID 10946429, compound → HCID 11077426, compound

Participants

Reaction Steps

A 500 ml autoclave was loaded in a glove box with 15.0 g (50.4 mmol) of (Z)-2-acetyl-1-(p-methoxybenzylidene)-1,2,3,4,5,6,7,8-octahydroisoquinoline, 170 ml of methanol and 3.9 mg (0.0050 mmol) of Ru(CH3COO)2 [(R)-HOBIPHEP] as the catalyst. The hydrogenation was carried out at 100° and 35 bar for 22 hours. The conversion was 98.5%. A 2 g product-containing aliquot of the hydrogenation solution was evaporated and the residue was dissolved in diethyl ether. The ether solution was filtered through a silica gel pad in order to separate the catalyst. Evaporation of the filtrate gave 1.97 g of (S)-2-acetyl-1-(p-methoxybenzyl)-1,2,3.4,5,6,7,8-octahydroisoquinoline as yellowish crystals of 95.9% e.e.

Provenance & Evidence