Tetra-n-butylammonium tribromide → HCID 59180118, compound

HRID 601949Notes

Reaction equation

HRID 601949 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:55]([CH:63]1[C:70]2[CH:69]=[C:68]([C:71]([O:73]C)=[O:72])[NH:67][C:66]=2[CH2:65][CH2:64]1)[CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>C(#N)C.O>[Br:1][C:69]1[C:70]2[CH:63]([CH2:55][CH2:56][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH2:64][CH2:65][C:66]=2[NH:67][C:68]=1[C:71]([OH:73])=[O:72]

Participants

5

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 59180061HCID 59180061, compound

Product 1

HCID 59180118HCID 59180118, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Tetrabutylammonium tribromide (114 mg, 0.24 mmol) was added to a solution of methyl 4-phenethyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (53 mg, 0.2 mmol) in 5 mL of acetonitrile at room temperature. After reacting overnight, the reaction was diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated with silica gel. Purification by column chromatography (Isco CombiFlash) eluting with a gradient of 0-30% EtOAc/heptane gave the title compound. 54.2 mg. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.69-1.80 (m, 1H), 2.10-2.22 (m, 2H), 2.56-2.71 (m, 4H), 2.72-2.83 (m, 1H), 3.00-3.09 (m, 1H), 3.80 (s, 3H), 7.11-7.16 (m, 1H), 7.17-7.21 (m, 2H), 7.22-7.27 (m, 2H); LCMS-MS (ESI+) 372.0 (M+Na).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated with silica gel
  6. customPurification by column chromatography (Isco CombiFlash)
  7. washeluting with a gradient of 0-30% EtOAc/heptane

Sources & evidence

ORD record
ord-62ffdb3b5f3844f39398fcdbb59e11f8
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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