1,2,3,4-Tetrahydroisoquinoline → 2-(3-Phenylisoxazol-5-yl)methyl-1,2,3,4-tetrahydroisoquinoline

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Reaction Steps

Prepared from 1,2,3,4-tetrahydroisoquinoline and 5-(bromomethyl)-3-phenylisoxazole under typical conditions. Purification by flash chromatography on silica gel 60, eluting with 25% EtOAc in hexane produced adduct 21A (81% yield). 1H NMR(300 MHz, CDCl3, δ): 7.83-7.80 (m, 2H), 7.48-7.40 (m, 3H), 7.16-7.11 (m, 3H), 7.08-6.99 (m, 1H), 6.57 (s, 1H), 3.91 (s, 2H), 3.76 (s, 2H), 3.00-2.80 (m, 4H). 13C NMR(300 MHz, CDCl3, δ): 170.25, 162.45, 134.04, 133.75, 129.97, 129.12, 128.92, 128.72, 126.81, 126.56, 126.36, 125.78, 101.26, 85.61, 53.20, 50.75, 29.03. MS(CI, NH3) m/e 291 (base, M+H+). HRMS(CI, NH3) m/e Calc'd for (M+H+): 291.1497. Found: 291.1512.

Provenance & Evidence