反应详情

A mixture of 1-formyl-cycloheptanecarboxylic acid methyl ester from Preparation 34 (35.6 mmol theoretical), sodium acetate (5.84 g, 72 mmol) and O-benzylhydroxylamine hydrochloride (11.36 g, 72 mmol) were stirred in methanol (71 mL) for 2 h. The methanol was removed in vacuo and the residue partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc (50 mL×5). The combined organic extracts were dried (MgSO4) and were evaporated in vacuo. Purifiaction by flash column chromatography using an eluting sytem of hexanes/EtOAc (99:1) provided the title compound as a clear colorless oil (5.22 g, 51%). MH+290.

1. customThe methanol was removed in vacuo
2. customthe residue partitioned between water and EtOAc
3. extractionThe aqueous phase was extracted with EtOAc (50 mL×5)
4. dry with materialThe combined organic extracts were dried (MgSO4)
5. customwere evaporated in vacuo