HCID 13919018, compound → HCID 53802334, compound

Participants

Reaction Steps

Into a Schlenk's tube which had previously been dried and purged with argon was weighed and charged 18.8 mg (0.0081 mmol) of [Ru((-)-T-BINAP)SnCl6 ]2NEt3 as a catalyst. Then, 40 ml of degassed anhydrous methanol was added thereto, and the solution was stirred in the presence of hydrogen at room temperature for 2 hours. Separately, a solution of 516 mg (1.82 mmols) of (Z)-N-formyl-1-(4-methoxyphenylmethylene)-3,4,5,6,7,8-hexahydroisoquinoline added to 20 ml of degassed anhydrous methanol was prepared. A fraction of 4.30 ml (molar ratio of substrate/catalyst =1000/1) was taken from the catalyst solution and mixed with a substrate solution. The mixture was transferred into an autoclave and stirred at 75° C. for 47 hours under a hydrogen pressure of 35 kg/cm2. After completion of the stirring, the reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 520 mg of (+)-N-formyl-1-(4-methoxyphenylmethylene)-1,2,3,4,5,6,7,8-octahydroisoquinoline. The yield was 100%.

Provenance & Evidence