(3E)-4-[(1S,3R)-3-[[[(1,1-Dimethylethyl)dimethylsilyl]oxy]methyl]-1,2,3,4-tetrahydro-1-methyl-5-isoquinolinyl]-2-methyl-3-buten-2-ol → 4-((1S,3R)-3-(((tert-Butyldimethylsilyl)oxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-2-methylbutan-2-ol

Participants

Reaction Conditions

Reaction Steps

Add a solution of (E)-4-[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl]-2-methyl-but-3-en-2-ol (68 g, 168.83 mmol) in ethanol (816 mL) to a pressure hydrogenation vessel and add 5% palladium on activated carbon (35.83 g, 16.84 mmol). Purge the vessel with hydrogen gas, pressurise to 470 kPa of hydrogen gas and stir at 25° C. After 16 hours, vent the vessel and filter the reaction mixture through diatomaceous earth. Wash the diatomaceous earth with ethyl acetate and concentrate the filtrate under reduced pressure to give an oil. Dissolve the oil in ethyl acetate (1 L) and concentrate under reduced pressure to give the title compound (64 g, 161 mmol). MS (m/z): 378.2 (M+1).

Provenance & Evidence