Tetrabutylammonium Fluoride → HCID 59563733, compound

HRID 1020143Notes

Reaction equation

HRID 1020143 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:32])[CH:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:14][O:15][Si](C(C)C)(C(C)C)C(C)C)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:15][CH2:14][CH:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:12]([NH:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH:1]=[N:2][CH:3]=[CH:4]2)=[O:32]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59563712HCID 59563712, compound

Product 1

HCID 59563733HCID 59563733, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To N-(isoquinolin-6-yl)-2-phenyl-3-(triisopropylsilyloxy)propanamide (E401) in THF cooled to 0° C. was added TBAF and this solution was stirred for 3 h at 0° C. The mixture was poured into EtOAc/NH4Cl(sat) and washed with NH4Cl(sat). The organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (0-10% MeOH/CH2Cl2) gave pure 3-hydroxy-N-(isoquinolin-6-yl)-2-phenylpropanamide (E402).

Workup

  1. washwashed with NH4Cl(sat)
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-63fb23bfa75b4fe493ef722c7c76b591
Source dataset
uspto-grants-2014_05
Patent number
US08716310B2

Reaction notes

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