Hydrochloric Acid → HCID 131720643, compound

Participants

Reaction Steps

A solution of 130 mg (0.40 mmol) of 3-(SR)-azido-2-(SR)-(4-fluorophenyl)-1-(SR)-(3,3-dimethoxy-1-oxo-propyl)cyclopentane (from Example 97, Step C) in 3 mL of pyridine was treated with 150 mg (2.2 mmol) of hydroxylamine×HCl and stirred at rt for 3 h. The reaction mixture was partitioned between 50 mL of ether and 25 mL of 2.0N HCl and the layers were separated. The organic layer was washed with 25 mL of sat'd NaHCO3, 25 mL of sat'd NaCl, dried over MgSO4 and concentrated in vacuo. A mixture of the crude ketoxime and 200 mg of Amberlyst 15 H+ resin in 4 mL of acetone was heated at reflux for 2 h. The mixture was cooled, the resin filtered and the filtrate concentrated in vacuo. Flash chromatography on 7 g of silica gel using 10:1 v/v hexanes/ether as the eluant afforded 79 mg (72%) of the title compound.

Provenance & Evidence