Styrene → HCID 54514540, compound

HRID 1379559Notes

Reaction equation

HRID 1379559 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13](Br)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18].C(N(CC)CC)C.[CH2:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CN(C)C=O>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:17])([C:7]3[CH:15]=[CH:14][C:13]([CH:26]=[CH:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:18]

Participants

7

Reactant 3

HCID 7501StyreneHCID 8471TriethylamineHCID 15355317(4aR)-(10bR)-4,10b-dimethyl-8-bromo-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Product 1

HCID 54514540HCID 54514540, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Five hundred mg of (4aR)-(10bR)-4,10b-dimethyl-8-bromo-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one, 4 mg of palladium acetate, 20 mg of tri-o-tolylphosphine, 0.34 mL of triethylamine and 5 mL of dimethylformamide were placed in a screw capped sealable tube with a stir bar. The mixture was warmed to 60° and then 200 mg of styrene was added and the vessel was flushed with argon. The vessel was then capped and heated at 120° for 24 h. The reaction mixture was cooled, diluted with ethyl acetate and filtered and the filtrate was concentrated under vacuum. The residue was dissolved in chloroform and washed twice with water. The organic layer was dried, filtered and evaporated under vacuum to obtain 400 mg of residue, which was recrystallized from ethyl acetate to obtain the desired product. m.p. 173°-175°. FDMS m/e=331.

Workup

  1. customcapped sealable tube with a stir bar
  2. temperatureThe mixture was warmed to 60°
  3. customthe vessel was flushed with argon
  4. customThe vessel was then capped
  5. temperatureheated at 120° for 24 h
  6. temperatureThe reaction mixture was cooled
  7. additiondiluted with ethyl acetate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under vacuum
  10. dissolutionThe residue was dissolved in chloroform
  11. washwashed twice with water
  12. customThe organic layer was dried
  13. filtrationfiltered
  14. customevaporated under vacuum

Sources & evidence

ORD record
ord-ead9ffe38e7b490080249952696c8017
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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