HCID 68688843, compound → HCID 68691468, compound

HRID 1296246Notes

Reaction equation

HRID 1296246 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:28][CH2:27][N:11]2[C:12](=[O:26])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH2:19][CH:20]=[CH2:21])=[CH:15][C:14]=3[C:22]([F:25])([F:24])[F:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:28][CH2:27][N:11]2[C:12](=[O:26])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH2:19][CH2:20][CH3:21])=[CH:15][C:14]=3[C:22]([F:24])([F:25])[F:23])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 68688843HCID 68688843, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68691468HCID 68691468, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-(2-propenyl)-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (27 mg, 0.07 mmol) and palladium on carbon (10 mg, 10 wt %; Aldrich) in methanol (1 mL) was subjected to 1 atmosphere of hydrogen for 50 min. The reaction was then filtered, concentrated, and the resulting residue was purified by radial chromatography (30% ethyl acetate in hexanes) to give the desired product as a clear residue (25 mg, 91%). MS (ESI) 399.4 (M+H).

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated
  3. customthe resulting residue was purified by radial chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4136f428d40f4426b01ea5d1af889656
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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