HCID 68688864, compound → HCID 68690573, compound

HRID 1159042Notes

Reaction equation

HRID 1159042 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:29][CH2:28][N:11]2[C:12](=[O:27])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH:19]=[C:20]([CH3:22])[CH3:21])=[CH:15][C:14]=3[C:23]([F:26])([F:25])[F:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:29][CH2:28][N:11]2[C:12](=[O:27])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:15][C:14]=3[C:23]([F:25])([F:26])[F:24])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 68688864HCID 68688864, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68690573HCID 68690573, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirring degassed solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-(2-methyl-1-propenyl)-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (60 mg, 0.15 mmol) and 10% palladium on carbon (5 mg) in MeOH (2 mL) was added hydrogen (1 atm). After 2 h, the reaction was filter and the solid washed with methanol. The organic layers were combined and conc. in vacuo to a colorless oil. The oil was purified by flash chromatography (silica gel, 0-50% EtOAc in hexanes) to give 28 mg of the desired product as a white solid. MS (ESI) 413 (M+H).

Workup

  1. filtrationthe reaction was filter
  2. washthe solid washed with methanol
  3. customThe oil was purified by flash chromatography (silica gel, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-94b731c550034d639935e5052fdf8b05
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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