Tetrabutylammonium Fluoride → [5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-2-(benzyloxy)phenyl]formamide

HRID 1925499Notes

Reaction equation

HRID 1925499 reaction equation
[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:33]4[CH:34]=[CH:35][C:36]([O:42][CH2:43][C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)=[C:37]([NH:39][CH:40]=[O:41])[CH:38]=4)[O:25][Si](C(C)(C)C)(C)C)=[CH:16][CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][NH:22][CH2:23][C@@H:24]([C:33]4[CH:34]=[CH:35][C:36]([O:42][CH2:43][C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)=[C:37]([NH:39][CH:40]=[O:41])[CH:38]=4)[OH:25])=[CH:18][CH:19]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86649158[5-((1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(benzyloxy)phenyl]-formamide

Product 1

HCID 86649159[5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-2-(benzyloxy)phenyl]formamideYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 25 (1.23 g, 1.44 mmol) in tetrahydrofuran (20 mL) was added tetrabutylammonium fluoride on silica gel (1-1.5 mmol/g, 2 g). The reaction mixture was stirred first at room temperature overnight and then at 45° C. for 3 hours. Silica was filtrated and the solvent was removed under reduced pressure. The crude was dissolved in ethyl acetate and the organic layer was washed several times with water. The solvent was removed under reduced pressure and the crude was purified by column chromatography with silica gel, eluting with chloroform/methanol (75:1) to give the title compound as a solid (0.36 g, 61%). MS (M+): 569.

Workup

  1. waitat 45° C. for 3 hours
  2. filtrationSilica was filtrated
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe crude was dissolved in ethyl acetate
  5. washthe organic layer was washed several times with water
  6. customThe solvent was removed under reduced pressure
  7. customthe crude was purified by column chromatography with silica gel
  8. washeluting with chloroform/methanol (75:1)

Sources & evidence

ORD record
ord-5150b122b37947479dff2e1ed302393a
Source dataset
uspto-grants-2012_05
Patent number
US08178679B2

Reaction notes

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