Ammonium formate → HCID 66905663, compound

HRID 1691671Notes

Reaction equation

HRID 1691671 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][C@@H:15]([CH2:18][OH:19])[C@H:14]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:13]2)[C:9]([F:26])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])=O.[NH4+]>O.CO.[Pd]>[F:26][C:9]1[C:10]([N:12]2[CH2:17][CH2:16][C@@H:15]([CH2:18][OH:19])[C@H:14]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:13]2)=[N:11][CH:2]=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 87198713HCID 87198713, compound

Product 1

HCID 66905663HCID 66905663, compoundYield 63.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 488 mg of methyl rel-2-chloro-5-fluoro-6-[(3R,4R)-4-(hydroxymethyl)-3-phenylpiperidin-1-yl]nicotinate, 428 mg of ammonium formate, and 12 mL of methanol was added 70 mg of 10% palladium/carbon while suspending it in 1 mL of water and 6 mL of methanol. The reaction mixture was vigorously stirred at 60° C. for 2 hours. After cooling to room temperature, the insolubles were filtered on a celite layer, and the filtrate was concentrated under reduced pressure. To the obtained residue was added chloroform, followed by washing with saturated aqueous sodium bicarbonate The organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 283 mg of methyl rel-5-fluoro-6-[(3R,4R)-4-(hydroxymethyl)-3-phenylpiperidin-1-yl]nicotinate as a colorless foamy substance.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe insolubles were filtered on a celite layer
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the obtained residue was added chloroform
  5. washby washing with saturated aqueous sodium bicarbonate The organic layer
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1fe539482c774723a2dc78b611cfce9b
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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