HCID 16115788, compound → HCID 16115384, compound

HRID 1296324Notes

Reaction equation

HRID 1296324 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][N:11]2[C:12](=[O:23])[C:13]3[C:18]([C:10]2=[C:9]1[CH3:26])=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:25][CH2:24][N:11]2[C:12](=[O:23])[C:13]3[C:18]([CH:10]2[CH:9]1[CH3:26])=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:21])([F:20])[F:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 16115788HCID 16115788, compound

Product 1

HCID 16115384HCID 16115384, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(t-butoxycarbonyl)-3,4-dihydro-1-methyl-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (0.20 g, 0.54 mmol) in methanol (10 mL) was added palladium on carbon (20 mg, 10 wt %; Aldrich). The resulting mixture was degassed (vacuum then argon, ×3) and subjected to a hydrogen atmosphere (60 psi) for 12 hr. The mixture was then filtered, and the filtrate was concentrated. The resulting residue was purified by flash column chromatography (SiO2, 0–50% ethyl acetate in hexanes) to afford N-(t-butoxycarbonyl)-(±)-1,3,4,10b-tetrahydro-1-methyl-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (0.19 g, 94%) as a white solid. MS (ESI) 371 (M+H).

Workup

  1. customThe resulting mixture was degassed (vacuum
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate was concentrated
  4. customThe resulting residue was purified by flash column chromatography (SiO2, 0–50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3cdd69d2e249487d8fd4557a28e30974
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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