Methanol → {1-[1-(3-Chlorophenyl)ethyl]cyclobutyl}(pyridin-2-yl)methanol

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Reaction Conditions

Reaction Steps

To a solution of Example 44C (0.5 g, 1.67 mmol) in 20 mL of methanol was added NaBH4 (0.076 g, 2 mmol) in small portions at 0° C. The mixture was stirred at 0° C. for 2 h. The mixture was concentrated and the residue was purified by prep TLC (petroleum ether: ethyl acetate=7:1) to afford the title compound (0.35 g, total yield 23.6%). 1H NMR (400 MHz, CDCl3): δ=8.58 (d, J=2.0 Hz, 1H), 7.65-7.62 (m, 1H), 7.27-7.12 (m, 6H), 4.78 (s, 1H), 4.16 (brs, 1H), 3.12-3.00 (m, 1H), 2.17-1.80 (m, 4H), 1.36 (d, J=6.0 Hz, 3H), 1.26-1.17 (m, 1H), 0.95-0.80 (m, 1H). LC-MS: m/z 302 (M+H).

Provenance & Evidence