4-Benzyl-4-piperidinol → (RS)-4-Benzyl-1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-hydroxy-propyl}-piperidin-4-ol

Participants

Reaction Steps

(RS)-tert-Butyl-dimethyl-(4-oxiranylmethyl-phenoxy)-silane (0.62 g, 2.34 mmol) was dissolved in MeOH (8 ml) and stirred overnight at room temperature in the presence of 4-benzyl-4-hydroxy-piperidine (0.9 g, 4.68 mmol). The reaction mixture was concentrated and the residue was chromatographed over silica gel (hexane-ethylacetate 1:1, then CH2Cl2 --MeOH 19:1) to provide (RS)-4-Benzyl-1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-hydroxy-propyl}-piperidin-4-ol (0.95 g, 90%) as a yellow oil, MS: m/e=456.5 (M+H+).

Provenance & Evidence