Ammonium formate → HCID 22279976, compound

HRID 1063422Notes

Reaction equation

HRID 1063422 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([CH:13]([O:16][CH:17]2[CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:20]([CH2:28][N:29](CC3C=CC=CC=3)CC3C=CC=CC=3)[CH2:19][O:18]2)[CH2:14][OH:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C([O-])=O.[NH4+]>CO>[NH2:29][CH2:28][CH:20]1[CH2:19][O:18][CH:17]([O:16][CH:13]([C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:44])[F:45])[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:6]=2)[CH2:14][OH:15])[CH:21]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formate2×HCID 22279980HCID 22279980, compound

Product 1

HCID 22279976HCID 22279976, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2SR, 3SR, 4SR, 2[(1′)]SR) 2-(3,5-Bis(trifluoromethyl)phenyl)-2-{4-[(N,N-dibenzylamino)methyl]-3-phenyl-tetrahydrofuran-2-yloxy}-ethanol (Description 9(a); 53 mg, 0.084 mmol) was dissolved in methanol (5 ml) and paladium on carbon (10 mg) and ammonium formate (37.1 mg) were added and the mixture refluxed for 1 hour. Further ammonium formate (20 mg) was added and the mixture refluxed for another hour. The catalyst was filtered off, the solvent was removed in vacuo and the residue purified using preparative TLC plates in 6% methanol in dichloromethane and 0.2% ammonia. The product was removed from the silica by washing with methanol (2×20 ml) and the solvent removed in vacuo. The residue was dissolved in dichloromethane (10 ml) and dried over MgSO4 to give the title compound (20.2 mg, 54%).

Workup

  1. temperaturethe mixture refluxed for 1 hour
  2. temperaturethe mixture refluxed for another hour
  3. filtrationThe catalyst was filtered off
  4. customthe solvent was removed in vacuo
  5. customthe residue purified
  6. customThe product was removed from the silica
  7. washby washing with methanol (2×20 ml)
  8. customthe solvent removed in vacuo
  9. dissolutionThe residue was dissolved in dichloromethane (10 ml)
  10. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-b835a78555a047148cc9b7475f709dde
Source dataset
uspto-grants-2005_11
Patent number
US06964981B2

Reaction notes

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