Hydrochloric Acid → (R)-4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidine

Participants

Reaction Steps

A mixture of (R)-tert-butyl 4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidine-1-carboxylate (8.2 g, 14.81 mmol) and 4M HCl (22.21 mL, 89 mmol) in dioxane in 1,4-Dioxane (5 mL) was stirred at room temp for 2 h. Mixture was then concentrated, diluted with ethyl acetate (100 mL), washed with 1N NaOH, dried (Na2SO4), filtered and concentrated to afford (R)-4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidine (6.35 g, 14.00 mmol, 95% yield) as viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.72-7.65 (m, 4H), 7.47-7.34 (m, 6H), 3.87 (sxt, J=5.9 Hz, 1H), 3.24 (t, J=6.4 Hz, 2H), 2.94-2.86 (m, 2H), 2.77-2.69 (m, 2H), 1.74-1.68 (m, 4H), 1.48-1.32 (m, 6H), 1.14 (s, 3H), 1.10-1.05 (m, 12H). LCMS (M+H)=454.2.

Provenance & Evidence