反应详情

1-(4-Benzyl-4-hydroxy-piperidin-1-yl)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propan-2-one (0.400 g, 0.88 mmol) was dissolved in THF (4 ml) and stirred for 16 hours at room temperature in the presence of 1N tetra-n-butylammonium fluoride (1 ml, 1 mmol). The reaction mixture was quenched with 20% NH4Cl (15 ml) and the aqueous phase was extracted with ethyl acetate (3×20 ml). Combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (ethyl acetate) to give a yellow oil which was dissolved in MeOH (2 ml) and treated with 1N HCl (0.5 ml). The solution was concentrated, the residue was dissolved in isopropanol (i-PrOH) and ether was added to provide 1-(4-Benzyl-4-hydroxy-piperidin-1-yl)-3-(4-hydroxy-phenyl)-propan-2-one hydrochloride (0.120 g, 36%) as white solid, m.p. 180°-181° C. and MS: m/e=340.3 (M+H+).

1. customThe reaction mixture was quenched with 20% NH4Cl (15 ml)
2. extractionthe aqueous phase was extracted with ethyl acetate (3×20 ml)
3. dry with materialCombined organic phases were dried over Na2SO4
4. concentrationconcentrated
5. customThe residue was chromatographed over silica gel (ethyl acetate)
6. customto give a yellow oil which
7. concentrationThe solution was concentrated
8. dissolutionthe residue was dissolved in isopropanol (i-PrOH)
9. additionether was added