Potassium Carbonate → HCID 18361973, compound

HRID 382818Notes

Reaction equation

HRID 382818 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].C[N:11]1[CH2:20][CH2:19][C@H:18]2[C@H:13]([C:14]3[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:15]=3[C:16](=[O:21])[CH2:17]2)[CH2:12]1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[CH3:27][C:22]1[C:15]2[C:16](=[O:21])[CH2:17][CH:18]3[CH:13]([C:14]=2[CH:25]=[C:24]([CH3:26])[CH:23]=1)[CH2:12][N:11]([C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3])[CH2:20][CH2:19]3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 870632,2,2-Trichloroethyl chloroformateHCID 86757549HCID 86757549, compound

Product 1

HCID 18361973HCID 18361973, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

a 2.1) 0.76 ml (5.65 mmol) of 2,2,2-trichloroethyl chloroformate was added at 1000 to a suspension of 500 mg (2.26 mmol) of (+)-cis-2,7,9-trimethyl-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one and 120 mg of K2CO3 in 20 ml of toluene and the mixture was heated at reflux for 16 hours. Subsequently, the solution was cooled to room temperature and poured on to 40 ml of ice-water. The aqueous phase was extracted twice with 50 ml of ethyl acetate, dried (MgSO4), filtered and evaporated. Chromatography of the residue (silica gel, hexane/ethyl acetate 4:1) yielded 890 mg (97%) of 2,2,2-trichloroethyl 7,9-dimethyl-6-oxo-3,4,4a,5,6,10b-hexahydro-1H-benzo[h]isoquinoline-2-carboxylate as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. extractionThe aqueous phase was extracted twice with 50 ml of ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-51c496f9efe549a299169af9c7bd2166
Source dataset
uspto-grants-2001_10
Patent number
US06310208B1

Reaction notes

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