Triphenylphosphine → 3-(1-t-butyloxycarbonyl-(2S)-azetidinylmethoxy)-6-chloropyridine

Participants

Reaction Steps

A 950 mg (5.1 mmol) sample of 1-t-butyloxycarbonyl-2-(S)-azetidinemethanol, prepared as in Example 7b above, and 550 mg (4.25 mmol) of 2-chloro-5-hydroxypyridine were reacted with triphenylphosphine and DEAD (5.1 mmol each) in 20 mL of THF according to the procedure of Example 14a, to give 1.09 g of the title compound. MS (DCI/NH3) m/e: 299/301 (M+H)+. 1H NMR (DMSO-d6, 300 MHz) δ: 8.14 (d, J=3.3 Hz, 1H), 7.48 (dd, J=8.8, 3.3 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 4.47-4.42 (m, 1H), 4.36 (dd, J=11.0, 4.4 Hz, 1H), 4.20 (dd, J=11.0, 3.3 Hz, 1H), 3.77 (t, J=7.7 Hz, 2H), 2.36-2.29 (m, 1H), 2.19-2.12 (m, 1H), 1.36 (s, 9H). [α]D25 =-67.3° (c=1.1, CHCl3).

Provenance & Evidence