Trifluoroacetic acid → HCID 16678725, compound

HRID 2105396Notes

Reaction equation

HRID 2105396 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[CH2:31][CH2:30][N:12]2[C:13]3[CH:14]=[CH:15][C:16]([O:20][CH:21]4[CH2:26][CH2:25][N:24]([CH:27]([CH3:29])[CH3:28])[CH2:23][CH2:22]4)=[CH:17][C:18]=3[CH:19]=[C:11]2[C:10]1=[O:32])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[OH:6][CH2:7][CH2:8][N:9]1[CH2:31][CH2:30][N:12]2[C:13]3[CH:14]=[CH:15][C:16]([O:20][CH:21]4[CH2:22][CH2:23][N:24]([CH:27]([CH3:29])[CH3:28])[CH2:25][CH2:26]4)=[CH:17][C:18]=3[CH:19]=[C:11]2[C:10]1=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68464869HCID 68464869, compound

Product 1

HCID 16678725HCID 16678725, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 0.145 g (0.30 mmol) 2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-(1-isopropyl-piperidin-4-yloxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one in 3 mL dichloromethane, 1 mL (1.49 g, 13 mmol) trifluoroacetic acid was added and the cooling bath was removed. The solution was evaporated and the residue was taken up in ethyl acetate and was washed with 1M aqueous sodium hydroxide solution and brine. The organic layer was dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) to give the desired compound as a white foam (88%).

Workup

  1. customthe cooling bath was removed
  2. customThe solution was evaporated
  3. washwas washed with 1M aqueous sodium hydroxide solution and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v)

Sources & evidence

ORD record
ord-f697ec2b934d4fe5b8ac6cb69817cb69
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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