Chloride → 1-[5-Benzyloxy-5-(4-fluoro-phenyl)-pentanoyl]-5-phenyl-pyrrolidin-2-one

HRID 1052895Notes

Reaction equation

HRID 1052895 reaction equation
[CH2:1]([O:8][CH:9]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].P([O-])([O-])([O-])=[O:32].C[NH2+:37][CH3:38].C[NH2+]C.C[NH2+]C.C(N([CH2:50][CH3:51])CC)C>O.CN(C)C=O>[CH2:1]([O:8][CH:9]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:10][CH2:11][CH2:12][C:13]([N:37]1[CH:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:51][CH2:50][C:38]1=[O:32])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 312ChlorideHCID 1140TolueneHCID 8471TriethylamineHCID 23179790Dimethyl ammonium phosphateHCID 667130465-Benzyloxy-5-(4-fluoro-phenyl)-pentanoic acid

Product 1

HCID 667135601-[5-Benzyloxy-5-(4-fluoro-phenyl)-pentanoyl]-5-phenyl-pyrrolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
22.5 °C

Procedure

10 gms of 5-Benzyloxy-5-(4-fluoro-phenyl)-pentanoic acid was added to 30 ml of toluene at 20-25° C., followed by 5.6 gms of triethyl amine and 5.5 gms of Pivollyl chloride. Reaction mass was stirred for about 2 hours. To the obtained reaction mass 6.5 gms of Evan's auxiliary and 20 ml of dimethyl ammonium phosphate and 0.2 gms of dimethyl formamide were added. Heated the reaction mass at reflux temperature and maintained for about 6-8 hours. Cooled the reaction mass to 20-25° C. and 20 ml of water was added. Stirred the reaction mass and separated the organic layer and aqueous layer was extracted with toluene. Combined all organic layers and washed with brine solution. Separated the organic layer and dried over sodium sulphate and distilled the solvent completely under reduced pressure at 50-55° C. The obtained oily mass was taken in toluene and hexane was added and stirred for about 1-2 hours at 0-5° C. Filtered the compound, washed with hexane and dried at 40-45° C. to get 12 gms of 1-[5-Benzyloxy-5-(4-fluoro-phenyl)-pentanoyl]-5-phenyl-pyrrolidin-2-one.

Workup

  1. customReaction mass
  2. customTo the obtained reaction mass 6.5 gms of Evan's auxiliary
  3. temperatureHeated the reaction mass
  4. temperatureat reflux temperature
  5. temperaturemaintained for about 6-8 hours
  6. stirringStirred the reaction mass
  7. customseparated the organic layer and aqueous layer
  8. extractionwas extracted with toluene
  9. washwashed with brine solution
  10. customSeparated the organic layer
  11. dry with materialdried over sodium sulphate
  12. distillationdistilled the solvent completely under reduced pressure at 50-55° C
  13. additionhexane was added
  14. stirringstirred for about 1-2 hours at 0-5° C
  15. filtrationFiltered the compound
  16. washwashed with hexane
  17. customdried at 40-45° C.

Sources & evidence

ORD record
ord-504a6025cd4a417c9e5461e4fc582ff9
Source dataset
uspto-grants-2016_07
Patent number
US09388440B2

Reaction notes

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