Tetrabutylammonium Fluoride → 2-Cyano-N-cyclopropyl-N-(2,3-dichlorobenzyl)-3-[4-(3-hydroxypropyl)phenyl]propanamide

HRID 561848Notes

Reaction equation

HRID 561848 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([C:35]#[N:36])[C:20]([N:22]([CH:32]2[CH2:34][CH2:33]2)[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=2[Cl:31])=[O:21])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:35]([CH:19]([CH2:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][OH:8])=[CH:17][CH:16]=1)[C:20]([N:22]([CH:32]1[CH2:34][CH2:33]1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=1[Cl:31])=[O:21])#[N:36]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 667617693-[4-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)phenyl]-2-cyano-N-cyclopropyl-N-(2,3-dichlorobenzyl)propanamide

Product 1

HCID 667616752-Cyano-N-cyclopropyl-N-(2,3-dichlorobenzyl)-3-[4-(3-hydroxypropyl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)phenyl]-2-cyano-N-cyclopropyl-N-(2,3-dichlorobenzyl)propanamide from the previous step (1 eq.) in THF (0.1 M) was added tetrabutylammonium fluoride (1.0 M THF solution, 1.5 eq.). The resulting reaction mixture was stirred at RT for 3 h. After quenching the reaction with 10% aq. HCl, the mixture was extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a pale yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. customAfter quenching
  3. customthe reaction with 10% aq. HCl
  4. extractionthe mixture was extracted with ether
  5. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customConcentration of the filtrate in vacuo afforded a pale yellow oil
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, 10:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-a875b3967d884433a2ac7feef7d028ca
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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