Ammonium formate → HCID 12085944, compound

HRID 397078Notes

Reaction equation

HRID 397078 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][N:16]2[C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[F:29][C:26]([F:27])([F:28])[C:25]([N:16]1[CH2:17][CH2:18][C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]1[C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)=[O:30]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18172401HCID 18172401, compound

Product 1

HCID 12085944HCID 12085944, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[1-(4-benzyloxyphenyl)-3,4-dihydro-1H-isoquinolin-2-yl]-2,2,2-trifluoroethanone (0.144 g, 0.35 mmol), ammonium formate (0.441 g, 7.00 mmol), and 20% Pd(OH)2/C (0.100 g) in MeOH (50 ml) was refluxed under N2 for 1.5 hr, then filtered through Celite. The filtrate was evaporated in vacuo to a yellow residue that was suspended in a mixture of H2O (15 ml) and saturated NaHCO3 solution (15 ml), then extracted with CHCl3 (4×15 ml). The combined organic extracts were dried over MgSO4 and concentrated in vacuo to give 0.115 g of colorless oil. Purification by flash chromatography, eluting with hexane:EtOAc (8:2) gave 0.100 g (89% yield) of colorless oil.

Workup

  1. temperaturewas refluxed under N2 for 1.5 hr
  2. filtrationfiltered through Celite
  3. customThe filtrate was evaporated in vacuo to a yellow residue that
  4. additionwas suspended in a mixture of H2O (15 ml) and saturated NaHCO3 solution (15 ml)
  5. extractionextracted with CHCl3 (4×15 ml)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4900891d1c24b93864b1e96d762dd44
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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