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

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Reaction Steps

(RS)-Toluene-4-sulfonic acid 6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl ester (1.32 g, 3.81 mmol) and 4-(methyl-benzyl)-piperidin-4-ol (3.13 g, 15.24 mmol) in mesitylene (100 ml) was heated at 140° C. for 20 hr. Following evaporation of the solvent the crude material was partioned between CH2Cl2 (50 ml) and 5% NaHCO3 (30 ml), the aqueous phase was extracted with CH2Cl2 (2×100 ml) washed with satd. NaCl solution (50 ml), dried (Na2SO4), filtered and evaporated. The crude product was chomatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-n-Hexane (1:3) then (1:1), to afford (RS)-1-(6-methoxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol as a white solid (972 mg, 2.56 mmol, 67.3%), Mp. 91-94° C., MS m/e=380.3 (M+H+).

Provenance & Evidence