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

HRID 642746노트

반응식

HRID 642746 반응식
[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

참가 물질

5

반응물 2

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

생성물 2

HCID 592595601-Oxo-octahydrocyclopenta[c]pyrrol-4-yl benzoateHCID 592595712-Oxo-octahydrocyclopenta[b]pyrrol-4-yl benzoate수율 133.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-ff4911748c5a40cb91eab397b5486820
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696241B2

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