Methanol → 8-((3aS,6aS)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-3-(phenylsulfonyl)-quinoline

HRID 2092194노트

반응식

HRID 2092194 반응식
[C:1]1([S:7]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:20]2[CH2:24][CH2:23][C@H:22]3[CH2:25][N:26](C(OCC)=O)[CH2:27][C@@H:21]23)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](I)(C)C.CO>C(Cl)(Cl)Cl>[N:20]1([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[N:12]=[CH:11][C:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:9])=[CH:19]3)[CH2:24][CH2:23][C@H:22]2[CH2:25][NH:26][CH2:27][C@@H:21]12

참가 물질

5

반응물 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 25196275(3aS,6aS)-ethyl 1-(3-(phenylsulfonyl)quinolin-8-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

생성물 1

HCID 251963888-((3aS,6aS)-hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-3-(phenylsulfonyl)-quinoline수율 22%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of (3aS,6aS)-ethyl 1-(3-(phenylsulfonyl)quinolin-8-yl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (60 mg, 0.133 mmol) and trimethylsilyl-iodide (160 mg, 0.797 mmol) in chloroform (1 mL) was stirred at reflux for 1.5 h. Methanol (4 mg) was added and the solution was partitioned between ethyl acetate and aqueous NaOH (1M). The organic extract was dried (MgSO4), filtered and concentrated to yield 11 mg (22%) of the title compound as a pale yellow oil.

후처리

  1. temperatureat reflux for 1.5 h
  2. customthe solution was partitioned between ethyl acetate and aqueous NaOH (1M)
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2d1669404e6949be95e2b2f745333d88
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08440694B2

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