Sodium borohydride → 5-({[6-(Bicyclo[2.2.1]hept-5-en-2-yl)hexyl]amino}methyl)quinolin-8-ol

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Reaction Steps

Imine 7 was dissolved in 50 mL of dry methanol and 1 equivalent of NaBH4 (0.136 g, 0.0036 mol) was added in small increments. After the addition was complete, the solution was allowed to stir for 10 minutes at room temperature. The solution was diluted with water and extracted three times with 20 mL of methylene chloride. The combined organic layers were washed with water, NaHCO3, brine, and dried over Na2SO4. The solvent was removed under reduced pressure to yield a brown liquid. Purification by column chromatography (silica gel, 4:1 hexanes/ethyl acetate, then pure ethyl acetate, then 5% methanol in ethyl acetate) gave the product as a pale yellow solid (0.658 g, 50%). 1H NMR (300 MHz, CDCl3) δ8.75 (1H, dd, J=1.09, 4.39); 8.51 (1H, dd, J=1.09, 8.24); 7.46 (1H, dd, J=4.39, 8.24); 7.38 (1H, d, J=7.69); 7.08 (1H, d, J=7.69); 6.11 (1H endo, dd, J=2.74, 5.49); 6.06–5.99 (2H exo, m); 5.90 (1H endo, dd, J=2.74, 5.49); 4.10 (1H, s); 2.73 (2H, s); 2.71 (2H, t, J=7.14); 1.99–1.02 (12H, m); 0.49–0.43 (1H, m). 13C NMR (75 MHz, CDCl3) δ151.8; 147.6; 137.0; 136.3; 133.4; 132.6; 128.0; 127.4; 126.8; 121.8; 109.2; 51.2; 50.0; 49.7; 45.5; 42.7; 38.9; 34.9; 32.6; 30.2; 29.9; 28.8; 27.5. Anal. Calcd for C23H30N2O: C, 78.88; H, 8.63; N, 8.00. Found C: 78.79, H: 8.72, N: 8.00.

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