Ammonium formate → (1S,2S,5R)-2-(7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione

HRID 425805Notes

Reaction equation

HRID 425805 reaction equation
C([N:8]1[CH2:15][C@H:14]2[C@H:10]([CH2:11][C:12]([F:17])([F:16])[CH2:13]2)[C@H:9]1[CH2:18][N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29])C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[F:17][C:12]1([F:16])[CH2:11][C@H:10]2[C@H:14]([CH2:15][NH:8][C@@H:9]2[CH2:18][N:19]2[C:20](=[O:29])[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]2=[O:28])[CH2:13]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59411625(1S,2S,5R)-2-(3-benzyl-7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 66703949(1S,2S,5R)-2-(7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dioneYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of (1S,2S,5R)-2-(3-benzyl-7,7-difluoro-3-azabicyclo[3.3.0]oct-2-ylmethyl)-isoindole-1,3-dione (1.73 g), Pd—C 10% (1.7 g) in dry MeOH (146 mL) was added ammonium formate (1.38 g). The reaction mixture was stirred at reflux for 16 h, cooled to RT and filtered over a pad of celite. The filtrate was concentrated in vacuo, partitioned between DCM/water. The aqueous phase was concentrated to yield 0.8 g (60%) of the title compound as a white solid

Workup

  1. temperatureat reflux for 16 h
  2. filtrationfiltered over a pad of celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompartitioned between DCM/water
  5. concentrationThe aqueous phase was concentrated

Sources & evidence

ORD record
ord-6a2034fbff2641cc89f6712ae7e39227
Source dataset
uspto-grants-2012_01
Patent number
US08106215B2

Reaction notes

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