1,2,3,4-Tetrahydroisoquinoline → HCID 9882311, compound

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Reaction Steps

Prepared in standard fashion from commercially available 4-chloro-2′-butyrothienone and 1,2,3,4-tetrahydroisoquinoline. Purified by flash chromatography, eluting with 1:1 EtOAc/hexane to provide 17A (58% yield) as a yellow oil. 1H NMR(300 MHz, CDCl3, δ): 7.72-7.70 (m, 1H), 7.60-7.58 (m, 1H), 7.15-6.98 (m, 5H), 3.62 (s, 2H), 3.01 (t, 2H, J=7 Hz), 2.87 (t, 2H, J=6 Hz), 2.72 (t, 2H, J=6 Hz), 2.59 (t, 2H, J=7 Hz), 2.10-2.00 (m, 2H). 13C NMR(300 MHz, CDCl3, δ): 193.10, 144.56, 134.92, 134.43, 133.34, 131.79, 128.64, 128.05, 126.59, 126.08, 125.58, 57.37, 56.10, 50.83, 37.01, 29.19, 22.14. . IR(KBr, cm−1): 1662 (s). UV (MeOH): max 282 nm, ε 260. MS(CI, NH3) m/e 286 (base, M+H ). HRMS(CI, NH3) m/e Calc'd for (M+H+): 286.1266. Found: 286.1259.

Provenance & Evidence