Potassium Carbonate → 1-{4-[5-(2-Fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester 3,3-dimethyl-2-oxobutyl ester

HRID 2407506Notes

Reaction equation

HRID 2407506 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([C:42]([OH:44])=[O:43])[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[N:28]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[C:31]([F:41])[CH:30]=4)[O:26][N:25]=3)=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:52][C:53](=[O:58])[C:54]([CH3:57])([CH3:56])[CH3:55]>CN(C)C=O>[CH3:55][C:54]([CH3:57])([CH3:56])[C:53](=[O:58])[CH2:52][O:43][C:42]([C:11]1([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]3[N:28]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=5)=[C:31]([F:41])[CH:30]=4)[O:26][N:25]=3)=[CH:22][CH:23]=2)[CH2:13][CH2:12]1)=[O:44]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21642BromopinacoloneHCID 595094311-{4-[5-(2-Fluorobiphenyl-4-yl)-[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester

Product 1

HCID 251267351-{4-[5-(2-Fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester 3,3-dimethyl-2-oxobutyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

50 mL N,N-dimethylformamide, 5 g of 1-{4-[5-(2-fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester, 1.8 g of anhydrous potassium carbonate and 2.3 mL of 1-bromo-3,3-dimethylbutan-2-one are added into a 3 neck round bottomed flask. The reaction mixture is heated to 55-60° C. and stirred for 20-60 min. After completion of reaction, the mixture is cooled to 25-30° C. and 100 mL of ice water are added. The slurry is stirred at 25-30° C. for about 30 min and filtered. The product is washed with 50 mL demineralized water, then by 20 mL isopropyl alcohol and suck dried for about 30 mins. Finally the product is dried at 35-40° C. under vacuum to yield 1-{4-[5-(2-fluorobiphenyl-4-yl)[1,2,4]oxadiazol-3-yl]benzyl}piperidine-4,4-dicarboxylic acid benzyl ester 3,3-dimethyl-2-oxobutyl ester.

Workup

  1. customAfter completion of reaction
  2. temperaturethe mixture is cooled to 25-30° C.
  3. stirringThe slurry is stirred at 25-30° C. for about 30 min
  4. filtrationfiltered
  5. washThe product is washed with 50 mL
  6. dry with materialby 20 mL isopropyl alcohol and suck dried for about 30 mins
  7. customFinally the product is dried at 35-40° C. under vacuum

Sources & evidence

ORD record
ord-72d35a4d4e004f60ab84a54c6246e193
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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