Potassium Carbonate → HCID 22874126, compound

HRID 1684544Notes

Reaction equation

HRID 1684544 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12](=[O:16])[O:13][C@@H:14]([CH3:15])[C@@H:7]1[CH2:6][CH2:5]2.Br[CH2:18][CH2:19][CH2:20][C:21]([F:24])([F:23])[F:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:15][C@H:14]1[C@@H:7]2[CH2:6][CH2:5][C:4]3[C:9]([N:8]2[C:12](=[O:16])[O:13]1)=[CH:10][CH:11]=[C:2]([O:1][CH2:18][CH2:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:3]=3

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 22874128HCID 22874128, compound

Product 1

HCID 22874126HCID 22874126, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 0.70 g (3.2 mmol) of cis-(±)-7-hydroxy-3-methyl-3,3a,4,5-tetrahydro-1H-oxazolo[3,4-a]quinolin-1-one in 15 ml of dimethylformamide are added 0.90 g (4.8 mmol) of 1-bromo-4,4,4-trifluorobutane and 0.90 g (6.4 mmol) of potassium carbonate. The mixture is heated at 90° C. for 4 hours and then diluted with ethyl acetate and washed with water. The organic phase is then dried over sodium sulphate and concentrated under reduced pressure, and the residue is chromatographed on a column of silica, with cyclohexane containing 20% of ethyl acetate. After trituration in diisopropyl ether, 0.80 g of product is obtained.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is then dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is chromatographed on a column of silica, with cyclohexane containing 20% of ethyl acetate

Sources & evidence

ORD record
ord-d51c2e8cb82644f3b2f25b2dc6668d40
Source dataset
uspto-grants-1997_06
Patent number
US05641785

Reaction notes

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