Реакция #43465

Уравнение реакции

compound 1H

6-Oxobicyclo[3.2.0]heptan-2-yl benzoate

O-mesitylenesulfonylhydroxylamine

→

title compounds 1I

1-Oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoate

1J

Выход 133.4%

2-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoate

Выход 133.4%

Растворители

CH2Cl2

CH2Cl2

Условия реакции

Обработка

1. 1
   КонцентрированиеIt was concentrated
2. 2
   workup.ADDITIONadded to a mixed solvent of benzene and methanol (30 mL, 3:1)
3. 3
   Другоеalumina solid was removed by filtration
4. 4
   ДругоеPurification by silica gel chromatography (5% to 100% EtOAc in hexanes

Методика

To a stirred solution of compound 1H (500 mg, 2.2 mmol) in CH2Cl2 (5 mL) was added a solution of O-mesitylenesulfonylhydroxylamine (650 mg, 3 mmol) in CH2Cl2 (2 mL) at −10° C., and the stirring was continued for 20 min between −10 to 0° C. It was concentrated, added to a mixed solvent of benzene and methanol (30 mL, 3:1) followed by a slurry of basic alumina (25 g) in methanol (20 mL). The reaction mixture was stirred at RT overnight, and alumina solid was removed by filtration. Purification by silica gel chromatography (5% to 100% EtOAc in hexanes, then 5% methanol in EtOAc) provide mixtures of the title compounds 1I and 1J (total 360 mg) as a yellow oil. MS (ES) m/z 246 [M+H]+.

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