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

HRID 857322Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-baf56986256541089dd764d4fa4962ac
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144913B2

Reaction notes

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