HCID 11639669, compound → HCID 66865277, compound

HRID 251880Notes

Reaction equation

HRID 251880 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](Cl)[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][C@H:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].[H][H]>[Pd].CO>[ClH:1].[CH3:13][N:7]1[CH2:6][C@@H:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:20]2[C:21](=[O:26])[CH2:22][CH2:23][C:24]2=[O:25])[C:4]2[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=2)[CH2:8]1

Participants

5

Reactant 2

HCID 11639669HCID 11639669, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66865277HCID 66865277, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a hydrogenation apparatus, a spatula-tip of palladium on activated carbon (5%) was added to a solution of 1-[2-((R)-6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]pyrrolidine-2,5-dione (68 mg, example 7) in methanol (15 ml), and, after application of a hydrogen atmosphere, agitated for 2 h. After the hydrogen had been removed, the apparatus was left to stand under argon overnight, and then the catalyst was filtered off and washed with methanol. The filtrate was concentrated to dryness. 10 mg of the crude product were taken up with water and 10% hydrochloric acid and freeze-dried. 10 mg of the title compound were obtained.

Workup

  1. customAfter the hydrogen had been removed
  2. waitthe apparatus was left
  3. filtrationthe catalyst was filtered off
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated to dryness
  6. customfreeze-dried

Sources & evidence

ORD record
ord-a3f6c192be124b038d8d2f048d2f4f9e
Source dataset
uspto-grants-2011_01
Patent number
US07868003B2

Reaction notes

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