HCID 68690613, compound → HCID 68691814, compound

HRID 1159064Notes

Reaction equation

HRID 1159064 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]([CH:10]2[CH2:9]1)=[CH:17][C:16]([C:19]([CH3:21])=[CH2:20])=[CH:15][C:14]=3[O:22][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]([CH:10]2[CH2:9]1)=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][C:14]=3[O:22][C:23]([F:25])([F:26])[F:24])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 68690613HCID 68690613, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68691814HCID 68691814, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirring degassed solution of N-(t-butoxycarbonyl)-(±)-1,3,4,10b-tetrahydro-9-isopropenyl-7-trifluoromethoxy-pyrazino[2,1-a]isoindol-6(2H)-one (67 mg, 0.16 mmol) and 10% palladium on carbon (5 mg) in MeOH (3 mL) was added hydrogen (1 atm). The reaction was stirred for 2 h and then filtered. The filtrate was conc in vacuo to a colorless oil. The oil was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes) to yield 67 mg of the desired product as a colorless oil. MS (ESI) 415 (M+H).

Workup

  1. filtrationfiltered
  2. customThe oil was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-78e825d009c74b279db755619e2358a8
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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