HCID 57550251, compound → HCID 57550255, compound

HRID 548643Notes

Reaction equation

HRID 548643 reaction equation
C([N:8]([CH2:16][C@H:17]1[N:21]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH:33]3[CH3:37])=[CH:24][CH:23]=2)[C:20](=[O:38])[CH2:19][CH2:18]1)CC1C=CC=CC=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[NH2:8][CH2:16][C@H:17]1[N:21]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH:33]3[CH3:37])=[CH:26][CH:27]=2)[C:20](=[O:38])[CH2:19][CH2:18]1

Participants

4

Reactant 1

HCID 57550251HCID 57550251, compound

Product 1

HCID 57550255HCID 57550255, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Palladium hydroxide on charcoal is added to a solution of (5S)-5-[(dibenzylamino)methyl]-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 112 (0.377 g, 0.74 mmol, 1 eq) in methanol (10 ml). The mixture is shaken overnight at room temperature under hydrogen atmosphere (45 psi). The mixture is filtered over celite and concentrated under vacuum. The residue is taken up in a mixture of methanol (10 ml) and 4 drops of aqueous 5 N hydrochloric acid. Palladium hydroxide on charcoal is added and the mixture is shaken again overnight at room temperature under hydrogen atmosphere (45 psi). The mixture is filtered over celite and concentrated under vacuum to give 0.245 g of (5S)-5-(aminomethyl)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 113 as a yellow oil.

Workup

  1. filtrationThe mixture is filtered over celite
  2. concentrationconcentrated under vacuum
  3. additionThe residue is taken up in a mixture of methanol (10 ml) and 4 drops of aqueous 5 N hydrochloric acid
  4. additionPalladium hydroxide on charcoal is added
  5. stirringthe mixture is shaken again overnight at room temperature under hydrogen atmosphere (45 psi)
  6. filtrationThe mixture is filtered over celite
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-aeeacd3392234607b5110118d55f85c8
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

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