Tributylstannane → 1,1,8-Triethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

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Reaction Conditions

Reaction Steps

To a stirred solution of compound 4 (103 mg, 0.35 mmol), AlBN (11 mg, 0.07 mmol, 0.2 eq), and toluene (3 mL) at room temperature under argon, HSnBu3 (380 μL, 1.41 mmol, 4.0 eq) was added in a dropwise manner. The resulting mixture was stirred overnight at 110° C. and concentrated. The residue was diluted with hexane and extracted three times with acetonitrile. The acetonitrile layers were combined, concentrated, and purified by column chromatography using 3:97:EtOAc:Hexane to give an off-white solid (56 mg, 62%): mp 133–134° C. 1HNMR (CDCl3, δ TMS): 0.88 (t, 6H), 1.37 (t, 3H), 1.87 (q, 4H), 2.78 (t, 2H), 2.86 (q, 2H), 4.02 (t, 2H), 7.01–7.38 (m, 3H, Ar—H), 7.46 (br, 1H, NH). MS−: m/z 256 ([M−H]−). Anal. (C17H23NO): C, H, N.

Provenance & Evidence