Sodium Hydroxide → HCID 16678929, compound

HRID 2105408Notes

Reaction equation

HRID 2105408 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[CH2:31][C@@H:30]([CH3:32])[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:33])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>ClCCl>[OH:6][CH2:7][CH2:8][N:9]1[CH2:31][C@@H:30]([CH3:32])[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:33]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 68464387HCID 68464387, compound

Product 1

HCID 16678929HCID 16678929, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 0.14 g (0.28 mmol) (R)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-(1-isopropyl-piperidin-4-yloxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one, 98 μL (0.89 g, 0.34 mmol) tetra-n-butylammonium fluoride solution (1M in tetrahydrofuran) was added. After 1 h, the reaction was diluted with dichloromethane and was poured on 1M aqueous sodium hydroxide solution. The organic phase was separated, washed with brine and dried over magnesium sulfate. After filtration the volatile components were removed at a rotary evaporator to give the desired product as a colorless oil (86%).

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration the volatile components
  5. customwere removed at a rotary evaporator

Sources & evidence

ORD record
ord-bbe1710fd48e4b539ba1a3cd8f64d475
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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