Iodine → (6R,9aS)-6-(4-carbomethoxyphenyl)-3-iodooctahydroquinolizin-4-one

HRID 553896Notes

Reaction equation

I[Si](C)(C)C.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:25][CH2:24][CH2:23][C@@H:22]3[N:17]2[C:18](=[O:26])[CH2:19][CH2:20][CH2:21]3)=[CH:12][CH:11]=1)([O:8][CH3:9])=[O:7].CN(C)CCN(C)C.[I:35]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:25][CH2:24][CH2:23][C@@H:22]3[N:17]2[C:18](=[O:26])[CH:19]([I:35])[CH2:20][CH2:21]3)=[CH:12][CH:11]=1)([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Iodotrimethylsilane (0.1 mL) was added to a solution of (6R*,9aS*)-6-(4-carbomethoxyphenyl)octahydroquinolizin-4-one (125 mg) and N,N,N′,N′-tetramethylethylenediamine (0.23 mL) in methylene chloride (10 mL) at 0° C., and the reaction solution was stirred at 0° C. for 30 minutes. Iodine (166 mg) was added to the reaction solution, which was then stirred at 0° C. for one hour. Ethyl acetate and a saturated sodium thiosulfate solution were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 180 mg of the title compound. The property value of the compound is as follows.

Workup

stirringwas then stirred at 0° C. for one hour
customthe organic layer was separated
washThe resulting organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e943fc5f4d4d495e950dddecab75e736
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048878B2

Reaction notes

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