Monoperoxyphthalic Acid Magnesium Salt → (+/-)-Ethyl [10-(4-chlorophenyl)-1-(methylsulfinyl)-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-9-yl]acetate

HRID 857322노트

반응식

HRID 857322 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[S:17][CH3:18])[N:10]3[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:9]=23)=[CH:4][CH:3]=1.C1C=C(C([O-])=[O:36])C(C(O[O-])=O)=CC=1.[Mg+2]>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[S:17]([CH3:18])=[O:36])[N:10]3[CH2:19][CH2:20][CH2:21][CH:22]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:9]=23)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 10130449Monoperoxyphthalic Acid Magnesium SaltHCID 91373095(+/-)-Ethyl [10-(4-chlorophenyl)-1-(methylsulfanyl)-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-9-yl]acetate

생성물 1

HCID 90857561(+/-)-Ethyl [10-(4-chlorophenyl)-1-(methylsulfinyl)-6,7,8,9-tetrahydro-pyrido[1,2-a]indol-9-yl]acetate

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

반응 조건

온도
0 °C

실험 절차

To a solution of the sulfide of Step 12 (110 mg, 0.1 mmol) in 8 ml of CH2Cl2/MeOH (10:1) at 0° C. was added MMPP (79 mg, 0.1 mmol). The reaction mixture was stirred at 0° C. for 1 hour and then quenched with a saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 70% EtOAc in Hexanes to provide 40 mg of the less polar diastereomer and 38 mg of the more polar diastereomer as a white solid.

후처리

  1. customquenched with a saturated aqueous solution of NaHCO3
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with 70% EtOAc in Hexanes
  7. customto provide 40 mg of the less polar diastereomer and 38 mg of the more polar diastereomer as a white solid

출처 및 근거

ORD 기록
ord-baf56986256541089dd764d4fa4962ac
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144913B2

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