Tetrabutylammonium Fluoride → 8-(benzyloxy)-5-(1-(hydroxy)-2-(2-methyl-1-(3-(2-(1-adamantyl)ethoxy)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-one

HRID 1925528Notes

Reaction equation

HRID 1925528 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([O:46][Si](C(C)(C)C)(C)C)[CH2:21][NH:22][C:23]([CH3:45])([CH3:44])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][C:34]34[CH2:43][CH:38]5[CH2:39][CH:40]([CH2:42][CH:36]([CH2:37]5)[CH2:35]3)[CH2:41]4)[CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:20]([OH:46])[CH2:21][NH:22][C:23]([CH3:44])([CH3:45])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH2:32][CH2:33][C:34]34[CH2:43][CH:38]5[CH2:37][CH:36]([CH2:42][CH:40]([CH2:39]5)[CH2:41]3)[CH2:35]4)[CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 675205018-(benzyloxy)-5-(1-(tert-butyldimethylsilyloxy)-2-(2-methyl-1-(3-(2-(1-adamantyl)ethoxy)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-one

Product 1

HCID 675205378-(benzyloxy)-5-(1-(hydroxy)-2-(2-methyl-1-(3-(2-(1-adamantyl)ethoxy)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-oneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 88 (0.748 g, 1.02 mmol) in tetrahydrofuran (15 mL) were added 0.546 g (1.73 mmol) of tetrabutylammonium fluoride. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the crude was partitioned between ethyl acetate and water. The organic layer was washed several times with water and the solvent was removed under reduced pressure. The crude was purified by column chromatography with silica gel, eluting with dichloromethane/methanol 90:4 to give 0.505 g (80% yield) of the title compound.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude was partitioned between ethyl acetate and water
  3. washThe organic layer was washed several times with water
  4. customthe solvent was removed under reduced pressure
  5. customThe crude was purified by column chromatography with silica gel
  6. washeluting with dichloromethane/methanol 90:4

Sources & evidence

ORD record
ord-7d7248ee4a894d248bb6c9eb2bfdfa4a
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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