Dimethyl Sulfoxide → 1-(4-Benzyl-4-hydroxy-piperidin-1-yl)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propan-2-one

Participants

Reaction Steps

To a solution of oxalylchloride (0.28 ml, 3.3 mmol) in CH2Cl2 (4 ml) at -78° C. was added dropwise dimethyl sulfoxide (DMSO) (0.47 ml, 6.6 mmol). After 30 min., a solution of (RS)-4-Benzyl-1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-hydroxy-propyl}-piperidin-4-ol (0.75 g, 1.65 mmol) in CH2Cl2 (4 ml) was added. After another hour at -78° C., triethylamine (1.8 ml, 13.2 mmol) was added and reaction mixture was allowed to warm up slowly to room temperature. After 1 hour, 20% NH4Cl (15 ml) was added, the resulting aqueous phase was extracted with CH2Cl2 (3×30 ml). Combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 1:1 then ethyl acetate) to provide 1-(4-Benzyl-4-hydroxy-piperidin-1-yl)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propan-2-one (0.4 g, 54%) as a yellow oil, and MS: m/e=454.5 (M+H+).

Provenance & Evidence