HCID 57847118, compound → HCID 57846922, compound

HRID 1009954Notes

Reaction equation

HRID 1009954 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 diisopropyl 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 diisopropyl ether

Sources & evidence

ORD record
ord-f8cac6e4d46d44e983dd2bc1de198761
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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