Methanol → (RS)-1-(6-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol

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Reaction Steps

To (RS)-1-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (843 mg, 2.22 mmol) in CH2Cl2 (20 ml) was added 1M BBr3/CH2Cl2 (4.88 ml, 4.88 mmol, 2.2 eq.) over 15 min at −78° C., the mixture was then allowed to warm to RT over 40 min. MeOH (3 ml), H2O (20 ml) and NaHCO3 (20 ml) were added and the mixture extracted with CH2Cl2 (4×50 ml). The extracts were washed with satd. NaCl solution (30 ml), dried (Na2SO4), filtered and evaporated, to afford the crude product as a yellow foam. Chromatography over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2—MeOH (97:3) afforded (RS)-1-(6-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol as a white foam (500 mg, 13.68 mmol, 61%), MS m/e=366.2 (M+H+).

Provenance & Evidence