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

Participants

Reaction Steps

A 169 mg sample (0.59 mmol.) of the product from step 23d above, 344 mg (2.07 mmol) of KI, 156 mg ((0.61 mmol) of I2, and 198 mg (2.36 mmol) of NaHCO3 were dissolved in 3 mL of water and 3 mL of THF. The mixture was heated at reflux for 6 hr, then cooled to room temperature. The mixture was diluted With 20 mL of 1.7M NaHSO3 solution, then extracted with ether. The combined extracts were washed with brine and dried over MgSO4, then concentrated to give 143 mg of crude product. Chromatography on silica gel, eluting with 20% ethyl acetate in hexane afforded 102 mg of the title compound after removal of the solvent.

Provenance & Evidence