4-Carbamoyl-3-(2-trifluoromethylphenyl)butanoic acid → 5-Hydroxy-3-(2-trifluoromethylphenyl)pentanoic acid amide

HRID 406378Notes

Reaction equation

HRID 406378 reaction equation
[C:1]([CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([F:19])([F:18])[F:17])[CH2:6][C:7](O)=[O:8])(=[O:3])[NH2:2].B#B.O1CCCC1>C(Cl)Cl>[OH:8][CH2:7][CH2:6][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]([F:17])([F:18])[F:19])[CH2:4][C:1]([NH2:2])=[O:3]

Participants

4

Reactant 2

HCID 666189254-Carbamoyl-3-(2-trifluoromethylphenyl)butanoic acidHCID 131714434Diborane tetrahydrofuran

Product 1

HCID 666189685-Hydroxy-3-(2-trifluoromethylphenyl)pentanoic acid amideYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Carbamoyl-3-(2-trifluoromethylphenyl)butanoic acid (646 mg) was dissolved in methylene chloride (32 mL), and a diborane-tetrahydrofuran solution (7.12 mL) was added at 0° C. After stirring at room temperature for two hours, the reaction solution was cooled to 0° C. The reaction was terminated with 1 N hydrochloric acid, followed by dilution with ethyl acetate. The organic layer was washed with 1 N sodium hydroxide and brine and dried over magnesium sulfate. Concentration under reduced pressure gave a crude product (388 mg) which was used for the next reaction without purification.

Workup

  1. temperaturethe reaction solution was cooled to 0° C
  2. customThe reaction was terminated with 1 N hydrochloric acid
  3. washThe organic layer was washed with 1 N sodium hydroxide and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-feea20bfc4984b829ae21dc0bd663b54
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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