O-Xylene → HCID 86591145, compound

HRID 350796Notes

Reaction equation

HRID 350796 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C@@H:22]3[CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26][C@@H:21]3[N:13]3[CH2:14][C:15](=O)[N:16]([CH3:19])[C:17]([CH:18]=1)=[C:12]23.B.C1COCC1.CC1C=CC=CC=1C.C=CCCCCCC>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C@@H:22]3[CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26][C@@H:21]3[N:13]3[CH2:14][CH2:15][N:16]([CH3:19])[C:17]([CH:18]=1)=[C:12]23

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 81251-OcteneHCID 2723981Borane;tetrahydrofuranHCID 86591146HCID 86591146, compound

Product 1

HCID 86591145HCID 86591145, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-3-methyl-2-oxo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (100 mg, 0.21 mmol) in THF (5.0 mL), BH3-THF (1M in THF) (0.82 mL, 0.82 mmol) was added dropwise. After addition was completed, the resulting reaction mixture was refluxed for 4 h, cooled to room temperature, and quenched cautiously with water (1.0 mL). The mixture was evaporated to dryness under reduced pressure and the residue obtained was treated with o-xylene (10 mL) and 1-octene (5 mL) and heated at reflux for 4 h. The reaction mixture was cooled to room temperature and concentrated to dryness under reduced pressure to give tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate as a white solid (50 mg, 58%).

Workup

  1. additionAfter addition
  2. customthe resulting reaction mixture
  3. temperaturewas refluxed for 4 h
  4. customquenched cautiously with water (1.0 mL)
  5. customThe mixture was evaporated to dryness under reduced pressure
  6. customthe residue obtained
  7. temperatureheated
  8. temperatureat reflux for 4 h
  9. temperatureThe reaction mixture was cooled to room temperature
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4a4f5c505d934c6bb73c6048fb152d40
Source dataset
uspto-grants-2007_02
Patent number
US07183282B2

Reaction notes

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