Triphenylphosphine → Tert-butyl 4-[4-(3,3,3-trifluoropropoxy)phenoxy]piperidine-1-carboxylate

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Reaction Steps

Diisopropyl azodicarboxylate (0.97 mL) was added to a solution of tert-butyl 4-(hydroxyphenoxy)piperidine-1-carboxylate (1.2 g), 3,3,3-trifluoro-1-propanol (0.56 g) and triphenylphosphine (1.5 g) in dichloromethane (15 mL). The reaction mixture was stirred at ambient temperature for 18 hours and then concentrated at reduced pressure. This resulting mixture was purified by silica column chromatography, eluting with a gradient of 0 to 15% ethyl acetate in hexane to give tert-butyl 4-[4-(3,3,3-trifluoropropoxy)phenoxy]piperidine-1-carboxylate as a white solid (0.6 g); NMR Spectrum: (CDCl3) 1.47 (s, 9H), 1.66-1.77 (m, 2H), 1.83-1.94 (m, 2H), 2.52-2.66 (m, 2H), 3.24-3.34 (m, 2H), 3.65-3.75 (m, 2H), 4.11 (t, 2H), 4.27-4.37 (m, 1H), 6.78-6.89 (m, 4H); Mass Spectrum: M+H+ 390 and (M-tBuOCO)+H+ 290.

Provenance & Evidence