Borane → HCID 24801135, compound

HRID 1715057Notes

Reaction equation

HRID 1715057 reaction equation
B.[F:2][C:3]1[CH:4]=[C:5]([S:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([CH2:22][CH2:23][C:24]([NH2:26])=O)=[CH:17][CH:16]=[CH:15]3)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1>C1COCC1>[F:2][C:3]1[CH:4]=[C:5]([S:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([CH2:22][CH2:23][CH2:24][NH2:26])=[CH:17][CH:16]=[CH:15]3)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 24801131HCID 24801131, compound

Product 1

HCID 24801135HCID 24801135, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane (8 mL of 1M THF solution) was added to a solution of 3-[6-(3-fluoro-benzenesulfonyl)-naphthalen-1-yl]-propionamide in 20 mL THF. The reaction mixture was refluxed for five hours, then cooled and quenched by addition of 10% aqueous HCl (25 mL). The mixture was heated to reflux for one hour, then cooled and THF was removed under reduced pressure. The resulting precipitate was collected by filtration to give 0.42 g of 3-[6-(3-Fluoro-benzenesulfonyl)-naphthalen-1-yl]-propylamine. MS (M+H)=344.

Workup

  1. temperatureThe reaction mixture was refluxed for five hours
  2. temperaturecooled
  3. customquenched by addition of 10% aqueous HCl (25 mL)
  4. temperatureThe mixture was heated
  5. temperatureto reflux for one hour
  6. temperaturecooled
  7. customTHF was removed under reduced pressure
  8. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-a7f879dcbc5240bf9fb2f25a52bec788
Source dataset
uspto-grants-2010_09
Patent number
US07799797B2

Reaction notes

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