(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline → (R)-N-(2,2,2-Trifluoroethyl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

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Reaction Steps

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (150 mg, 541 μmol, Example 87, Step 3) in MeCN (2 mL) was added 4-nitrophenyl 2,2,2-trifluoroethylcarbamate (286 mg, 1082 μmol). The resulting mixture was then subjected to a microwave irradiation at 100° C. for 15 min. Then, the solvent was removed and the residue was dissolved in a solution of DMSO and MeOH (1:1, 2 mL). The solution mixture was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the desired product, which was then dissolved in MeOH (2.0 mL). The solution was then washed through PL-HCO3 MP-resin and the resin was then washed with MeOH (2×2 mL). The combined washings were concentrated and dried under vacuum to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 403 (M+H).

Provenance & Evidence