Reaktion #43465

Reaktionsgleichung

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

Ausbeute 133.4%

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

Ausbeute 133.4%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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]+.

Quelle