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

HRID 857322ノート

反応式

HRID 857322 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-baf56986256541089dd764d4fa4962ac
出典データセット
uspto-grants-2006_12
特許番号
US07144913B2

反応ノート

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