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

Participants

Reaction Steps

Triphenylphosphine (917 mg) was added to a solution of N-tert-butoxycarbonyl-4-hydroxypiperidine (A, 704 mg), 4-benzyloxyphenol (700 mg) and diethyl azodicarboxylate (609 mg) in tetrahydrofuran (20 mL) at room temperature. After stirring at room temperature for 14 hr, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, v/v) to give the titled compound (703 mg) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 1.72 (m, 2H), 1.88 (m, 2H), 3.29 (ddd, J=3.9, 7.8, 12.5 Hz, 2H), 3.70 (m, 2H), 4.32 (quintet, J=3.9 Hz, 1H), 5.01 (s, 2H), 6.84-6.91 (m, 4H), and 7.32-7.43 (m, 5H).

Provenance & Evidence