Citric Acid → 4-(2-Hydroxyethyl)-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile

HRID 420605Notes

Reaction equation

HRID 420605 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][C:9]1([C:28]#[N:29])[CH2:14][CH2:13][N:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:11][CH2:10]1)(C)(C)C.[F-].C[N+](C)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[OH:6][CH2:7][CH2:8][C:9]1([C:28]#[N:29])[CH2:14][CH2:13][N:12]([C:15]2[S:16][C:17]3[CH:23]=[C:22]([C:24]([F:26])([F:27])[F:25])[CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 311Citric AcidHCID 67803Tetramethylammonium fluorideHCID 579664524-[2-(t-Butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile

Product 1

HCID 579665674-(2-Hydroxyethyl)-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrileYield 95%

Conditions

Temperature
0 °C

Procedure

To 4-[2-(t-butyldimethyl silyloxy)ethyl]-1-(6-trifluoromethyl benzothiazole-2-yl)piperidine-4-carbonitrile (510 mg) was added tetramethylammonium fluoride (1 M tetrahydrofuran solution, 1.63 mL). The mixture was stirred at 0° C. for 0.5 hour. To the reaction solution was added aqueous citric acid solution and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatograph on silica gel to give the title compound (366 mg). Yield: 95%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatograph on silica gel

Sources & evidence

ORD record
ord-3f30962b45294306898de9dec91c9712
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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