Trimethyl orthoformate → 3-Methyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

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(R)—N-((2-(2,2-Dimethoxypropyl)phenyl)(4-(trifluoromethyl)phenyl)methyl)-2-methylpropane-2-sulfinamide (6.650000 g, 15 mmol) was dissolved in 150 mL of DCE and hydrogen chloride, 4.0 m solution in 1,4-dioxane (11 mL, 44 mmol) was added. Stirring was continued for 20 min and trimethyl orthoformate (8.0 mL, 73 mmol) and sodium triacetoxyborohydride (11 g, 51 mmol) were added. TLC-analysis showed a complex product mixture but LCMS showed the formation of some desired product along with a lot of fully aromatized product. The crude was semi-purified via glass colm chrom and used w/o further clean up in the next steps. MS (ESI, positive ion) m/z: 292.0 (M+1)

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