Sodium borohydride → 1-(4-{4-[2(S),3-dihydroxy-propoxy]-3-methylphenyl}-4-[4-(2-hydroxy-3,3-dimethylbutoxy)-3-methylphenyl]piperidin-1-yl)ethanone

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Reaction Steps

To a solution of 1-(4-{1-acetyl-4-[4-(2,3-dihydroxypropoxy)-3-methylphenyl]-piperidin-4-yl}-2-methylphenoxy)-3,3-dimethylbutan-2-one (0.14 g, 0.28 mmol) in anhyd MeOH (3 mL) cooled to 0° C. was added sodium borohydride (11 mg, 0.29 mmol). After 8 h the reaction was quenched with water and extracted with EtOAc (2×20 mL). The combined extracts were washed with brine, dried (anhyd Na2SO4), concentrated under reduced pressure and purified by reverse-phase HPLC (C18 column), eluting with 0.05% TFA in MeCN—H2O (1:9 to 9:1) to provide the title compound (0.10 g, 73%) as a white solid: 1H-NMR (CDCl3) δ 6.96-7.01 (4H, m), 6.74 (2H, d, J=8.3), 4.05-4.14 (2H, m), 4.03 (2H, m), 3.82-3.88 (2H, m), 3.74-3.80 (1H, dd, J=5.3, 11.4), 3.67-3.71 (1H, dd, J=2.8, 8.6), 3.64 (2H, m), 3.47 (2H, m), 2.27-2.36 (4H, m), 2.19 (3H, s), 2.18 (3H, s), 2.08 (3H, s), 1.00 (9H, s).

Provenance & Evidence