O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → 2-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoate

HRID 15187

Reaktionsgleichung

Reaktionsgleichung von HRID 15187
[C:1]([O:9][CH:10]1[CH2:16][CH2:15][CH:14]2[CH:11]1[CH2:12][C:13]2=[O:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:30])(=O)=O>C(Cl)Cl>[C:1]([O:9][CH:10]1[CH:11]2[CH:14]([C:13](=[O:17])[NH:30][CH2:12]2)[CH2:15][CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:1]([O:9][CH:10]1[CH:11]2[CH:14]([NH:30][C:13](=[O:17])[CH2:12]2)[CH2:15][CH2:16]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 592595756-Oxobicyclo[3.2.0]heptan-2-yl benzoate

Produkt 2

HCID 592595601-Oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoateHCID 592595712-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoateAusbeute 133,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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]+.

Aufarbeitung

  1. concentrationIt was concentrated
  2. additionadded to a mixed solvent of benzene and methanol (30 mL, 3:1)
  3. customalumina solid was removed by filtration
  4. customPurification by silica gel chromatography (5% to 100% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-69d09e97128d4e6b92c02884fe908ded
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732480B2

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