Hydrochloric Acid → 4-Phenyl-4-[(1-(3,5-bis(trifluoromethyl)Phenyl)-1-hydroxymethyl-2-hydroxyethoxy)methyl]piperidine Hydrochloride

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Reaction Conditions

Reaction Steps

The oil from step (a) above was dissolved in anhydrous tetrahydrofuran (50 ml) and lithium borohydride (0.140 g, 6.5 mmol) was added. The reaction was stirred at 25° C. for 30 minutes and quenched with saturated aqueous ammonium chloride solution (75 ml) and extracted into ethyl acetate (75 ml). The organic layer was dried over (MgSO4) and removed in vacuo. The residue was dissolved in ethanol (15 ml) and hydrogenated at 50 psi over Pd(OH)2 (0.150 g) for 16 h. The catalyst was filtered and the solvent evaporated. The residue was chromatographed on silica eluting with ethyl acetate. The oil obtained was treated with ethereal HCl and left standing for 16 h. The solid formed was filtered off and washed with ether to obtain the title compound. 1H NMR (DMSO-d6) δ 7.99 (1 H, s), 7.75 (2H, s), 7.48 (4H, m), 7.35 (1H. m), 3.85 (4H, s), 3.47 (2H, s), 3.33 (2H, br d), 2.97 (2H, br t), 2.56 (2H, br d), 2.10 (2H, br t). MS (Cl+) 478 [M+H]+.

Provenance & Evidence