Triphenylphosphine → 3-(1-BOC-2-(S)-azetidinylmethoxy)-5-bromo-6-chloropyridine

Participants

Reaction Steps

To a solution of diethyl azodicarboxylate (1.52 mL, 9.6 mmol) in THF (56 mL) was added triphenylphosphine (2.52 g, 9.6 mmol) at 0° C., and the reaction mixture was stirred for half an hour. 1-BOC-2-(S)-azetidinemethanol (1.44 g, 7.7 mmol) and 5-bromo-6-chloropyridine-3-ol (1.4 g, 6.4 mmol; prepared according to V. Koch and S. Schnatterer, Synthesis 1990, 499-501)) were then added. The reaction mixture was slowly warmed up to room temperature overnight. Solvent was removed, and the residue was chromatographed on a silica gel column, eluting with chloroform:methanol 100:1 to afford the title compound. MS (DCI/NH3) m/z 377, 379 (M+H)+.

Provenance & Evidence