反応 #43465

反応方程式

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

収率 133.4%

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

収率 133.4%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

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

実験手順

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]+.

出典