Iodine → 3-Methyl-5-(1-CBZ-2(S)-pyrrolidinyl)isoxazole

Participants

Reaction Steps

To a stirred solution of 6 g (20.83 mmol) of the oxime compound from step 24f above, in a wrapped flask to protect from light, was added 12.1 g (72.92 mmol) of Kl dissolved in 80 mL of water and, in small portions, 7 g (83.33 mmol) of NaHCO3 and 15.86 g (62.5 mmol) of iodine. The reaction was heated at reflux for 16 hr, cooled and diluted with saturated aq. NaHSO3. The solution was extracted with ether, and the extract was washed with saturated aq. NaHSO3, dried over Na2SO4, and concentrated to afford the title product (5.06 g, 85% yield). The compound was taken to the next step without further purification. IR 1702, 1604, 1444, 1417, 1356, 1173, 1103, 1079 cm-1.

Provenance & Evidence