Methanol → (RS)-2-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-ylmethyl]-2,3-dihydro-1H-indol-5-ol

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Reaction Steps

To (RS)-1-(5-methoxy-2,3-dihydro-1H-indol-2-ylmethyl)-4-(4-methyl-benzyl)-piperidin-4-ol (131 mg, 0.357 mol) in CH2Cl2 (10 ml) was added 1M BBr3—CH2Cl2 (2.14 ml, 2.74 mmol, 6 eq.) at −78° C. over 5 min. The reaction was stirred at RT for 48 hr., then MeOH (20 ml) was added followed by 10% NaHCO3 (20 ml), and the aqueous phase extracted with CH2Cl2 (2×50 ml) and the combined extracts washed with satd. NaCl solution (50 ml), dried over (Na2SO4) filtered and evaporated. Purification of the crude product over SiO2 (Merck 230-400 mesh) eluting with CH2Cl2-MeOH (9:1) afforded (RS)-2-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-ylmethyl]-2,3-dihydro-1H-indol-5-ol as a brown solid (64.6 mg, 0.183 mmol, 51%), Mp. 90-94° C., MS: m/e=353.3 (M+H+).

Provenance & Evidence