Triphenylphosphine → tert-Butyl (2S,4S)-4-azido-2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

To a stirred mixture of tert-butyl (2S,4R)-4-hydroxy-2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate (3.00 g, 11.6 mmol, step 2 of Example 9) in tetrahydrofuran (50 mL) were added triphenylphosphine (4.55 g, 17.4 mmol) and diethyl azodicarboxylate solution (50% in toluene, 7.56 mL, 17.36 mmol) at room temperature. After stirring for 15 min, diphenyl phosphoryl azide (3.74 mL, 17.36 mmol) was added to the mixture. The resulting mixture was stirred at room temperature for 40 h and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (4:1) to give 2.53 g (77%) of the title compound as a pale yellow oil.

Provenance & Evidence