HCID 57847118, compound → HCID 57846922, compound

HRID 550313Notes

Reaction equation

HRID 550313 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C@H:6]2[C@H:15]3[CH2:16][CH2:17][N:18]([C:19]([C@H:21]4[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]4[NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:20])[C@H:14]3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7]2)=[CH:2]1.S1C=CC([C@H]2[C@@H]3CCN(C([C@H]4CCCC[C@H]4NC(=O)C4C=CC=CC=4)=O)[C@@H]3C3C=CC=CC=3N2)=C1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:15]3[CH2:16][CH2:17][N:18]([C:19]([C@H:21]4[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]4[NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:20])[C:14]=3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]=2)=[CH:2]1

Participants

5

Reactant 2

HCID 57847118HCID 57847118, compoundHCID 68576547HCID 68576547, compound

Product 1

HCID 57846922HCID 57846922, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

A mixture of N-((1R,2S)-2-{[(3aR*,4R*,9bR*)-4-(3-thienyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)benzamide and N-((1R,2S)-2-{[(3aS*,4R*,9bS*)-4-(3-thienyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexyl)benzamide (422 mg, 0.87 mmol) was dissolved in toluene (30 ml), manganese dioxide (7.6 g, 87 mmol) was added and the mixture was refluxed overnight. The reaction mixture was filtered through celite and washed with methanol. The filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography using silica gel (30 g), and eluted with hexane-ethyl acetate (9:1-2:1, v/v). Crystallization from diisopropy ether gave the title compound (70 mg, 17%) as pale-brown crystals.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. washeluted with hexane-ethyl acetate (9:1-2:1
  6. customCrystallization from diisopropy ether

Sources & evidence

ORD record
ord-f7ea283eec4c4c9abcdd6b385ef3f028
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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