Ammonium formate → HCID 57513871, compound

HRID 251474Notes

Reaction equation

HRID 251474 reaction equation
[CH2:1]([N:8]1[C:16]2([CH:21]=[CH:20][NH:19][CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH2:1]([N:8]1[C:16]2([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57513870HCID 57513870, compound

Product 1

HCID 57513871HCID 57513871, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (1 g) was added to a stirred solution of 2-benzyl-2′,3′-dihydro-1′H-spiro[isoindoline-1,4′-pyridin]-3-one 2a (2 g, 6.9 mmol) and ammonium formate (8.7 g, 138 mmol) in ethanol (50 mL). The mixture was heated under reflux for 3 hr then cooled to room temperature. The solution was filtered through Celite and the filtrate was concentrated to give a white solid. The solid was washed with ethyl acetate (4×25 mL) and the washings were concentrated to give 2-benzylspiro[isoindoline-1,4′-piperidin]-3-one 2b as a yellow oil (2.0 g, 99%). FIA m/z [M+H]+ 293.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. filtrationThe solution was filtered through Celite
  4. concentrationthe filtrate was concentrated
  5. customto give a white solid
  6. washThe solid was washed with ethyl acetate (4×25 mL)
  7. concentrationthe washings were concentrated

Sources & evidence

ORD record
ord-636bab1528f44b26a7454d0b4e6562f6
Source dataset
uspto-grants-2011_01
Patent number
US07863449B2

Reaction notes

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