Triphenylphosphine → (S)-Tert-butyl 2-(((5-bromopyridin-3-YL)oxy)methyl)azetidine-1-carboxylate

Participants

Reaction Steps

A 619.3 mg (3.31 mmol) sample of 1-BOC-2-(S)-azetidinemethanol, prepared as in Example 7b above, and 480 mg (2.76 mmol) of 5-bromo-3-hydroxypyridine, from Example 65b above, were reacted with triphenylphosphine and DEAD (3.31 mmol each) in 10 mL of THF according to the procedure of Example 14a, to give 887 mg of the title compound. MS (DCI/NH3) m/e 243/246 (M+H)+, 260/262 (M+NH4)+. 1H NMR (CDCl3, 300 MHz) δ: 8.35-8.25 (br, 2H), 7.44 (s, 1H), 4.55-4.47 (m, 1H), 4.39-4.29 (m, 1H), 4.16-4.10 (m, 1H), 3.98-3.85 (m, 2H), 2.42-2.33 (m, 2H), 1.42 (s, 9H).

Provenance & Evidence