Borane;tetrahydrofuran → HCID 68534451, compound

HRID 1991562Notes

Reaction equation

HRID 1991562 reaction equation
B.C1COCC1.[CH2:7]([C:12]1[CH:13]=[C:14]([C:24]([NH2:26])=O)[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:16][CH:17]=1)[C:8]([CH3:11])([CH3:10])[CH3:9]>>[CH2:7]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:14]([CH2:24][NH2:26])[CH:13]=1)[C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 58909288HCID 58909288, compound

Product 1

HCID 68534451HCID 68534451, compoundYield 105.2%

Procedure

To borane-THF (1M, 1.7 mL, 1.7 mmol) was added 4-neopentyl-1,1′-biphenyl-2-carboxamide (200 mg, 0.75 mmol), and the reaction stirred at reflux 16 h. The solution was cooled and quenched with 1N HCl. The solution was basified with saturated sodium bicarbonate, and the product was extracted into ethyl acetate. The organics were washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated in vacuo to give the title compound as an oil (200 mg). ESI MS m/z 254.22 [M+H]+.

Workup

  1. temperatureat reflux 16 h
  2. temperatureThe solution was cooled
  3. customquenched with 1N HCl
  4. extractionthe product was extracted into ethyl acetate
  5. washThe organics were washed with saturated sodium chloride
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58e0d6395a96487f903fc4e53094f74d
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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