Dimethyl Sulfoxide → methyl (1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-methyl-1,2,3,4-tetrahydroisoquinoline-5-carboxylate

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Reaction Conditions

Reaction Steps

In a glass pressure vessel, containing a magnetic stirrer bar, suspend (1S,3R)-5-bromo-3-((tert-butyldimethylsilyloxy)methyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline (30 g, 81.0 mmol), palladium acetate (1.8 g, 8.1 mmol), bis-(1,3-diphenylphosphino)propane (6.7 g, 16.2 mmol) and sodium carbonate (34.3 g, 324.0 mmol) in a mixture of dimethyl sulfoxide (360 mL) and methanol (180 mL). Charge the vessel with carbon monoxide (410 kPa) and warm to 100° C. with stirring. Maintain temperature at 100° C. for 19 hours. Allow the mixture to cool to ambient temperature. Filter the resulting suspension and dilute the filtrate with methyl tert-butyl ether (1000 mL). Wash the solution with brine (3×500 mL). Dry over sodium sulfate, filter and concentrate under reduced pressure to yield the title compound as a dark orange oil (26.7 g, 76.4 mmol): MS (m/z): 350.0 (M+1).

Provenance & Evidence