Tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate → Tert-butyl 4-hydroxypiperidine-1-carboxylate

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Reaction Steps

To 10% palladium on carbon (0.75 g), under a stream of argon, was added a solution of tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate (7.5 g) in ethanol (250 mL). The vessel was purged with argon three times, before hydrogen was introduced to the system via a balloon. The reaction was stirred vigorously at ambient temperature for 3 hours. Hydrogen was removed from the system and purged three times with argon before filtering through a celite pad. The pad was washed thoroughly. The filtrate and washings were combined and evaporated, the solid triturated with 20% diethyl ether/iso-hexane to yield tert-butyl-4-hydroxy-1-piperidinecarboxylate (5.7 g) NMR Spectrum: (CDCl3) 1.5 (s, 9H), 1.7 (m, 2H), 1.9 (m, 2H), 3.3 (m, 2H), 3.7 (m, 2H), 4.3 (m, 1H), 4.8 (s, 1H), 6.7 (m, 4H).

Provenance & Evidence