Dimethyl Sulfide → (S)-2,2,2-trifluoro-1-(6-hydroxy-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)ethanone

Participants

Reaction Steps

To a solution of (R)-2-methyl-CBS-oxazaborolidine (1M solution in toluene, 0.56 mL, 0.56 mmol) in 15 mL of toluene at −10° C. was added BH3.SMe2 (1.27 mL, 13.38 mmol). To this stirred solution was then added 2-(2,2,2-trifluoroacetyl)-1,2,3,4,8,9-hexahydrobenzo[g]-isoquinolin-6(7H)-one(3.31 g, 11.15 mmol)in 5 mL of dry THF dropwise while keeping the temperature around −10° C. After stirring at room temperature for 2 h, the reaction mixture was cooled down to −10° C. and was quenched with 6 mL of MeOH and was then evaporated to dryness and directly submitted to flash chomatography (SiO2, hexane/EtOAc=3:1 to 2:1 to 1:1) to afford (S)-2,2,2-trifluoro-1-(6-hydroxy-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)ethanone as a white solid.

Provenance & Evidence