Tetrabutylammonium Fluoride → alpha-(3,4-Dimethoxvphenyl)-3.4-dihydro-7-hydroxy-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile

HRID 1078752Notes

Reaction equation

HRID 1078752 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([S:39][C:40]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([O:31][Si](C(C)(C)C)(C)C)=[C:24]([O:29][CH3:30])[CH:25]=3)[CH2:20]2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([S:39][C:40]2[CH:41]=[CH:42][C:43]([CH3:46])=[CH:44][CH:45]=2)([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([OH:31])=[C:24]([O:29][CH3:30])[CH:25]=3)[CH2:20]2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15285555alpha-(3,4-Dimethoxyphenyl)-7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,4-dihydro-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrile

Product 1

HCID 10721301alpha-(3,4-Dimethoxvphenyl)-3.4-dihydro-7-hydroxy-6-methoxy-alpha-[(4-methylphenyl)thio]-2(1H)-isoquinolineheptanenitrileYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.0 g of α-(3,4-dimethoxyphenyl)-7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,4-dihydro-6-methoxy-α-[(4-methylphenyl)thio]-2(1H) isoquinolineheptanenitrile in 30 mL of tetrahydrofuran is added 3.02 mL of a 1.0M solution of tetrabutylammonium fluoride in tetrahydrofuran. This is sealed and stirred for 5 hours. The reaction mixture is evaporated and the residue taken up in ethyl acetate. The solution is washed three times with water, and the organic phase is separated and evaporated. The gum remaining is redissolved in chloroform and the solution evaporated in vacuo at 66° C. This process is repeated twice more affording 0.83 g of the desired product as a brown gum.

Workup

  1. customThis is sealed
  2. customThe reaction mixture is evaporated
  3. washThe solution is washed three times with water
  4. customthe organic phase is separated
  5. customevaporated
  6. dissolutionThe gum remaining is redissolved in chloroform
  7. customthe solution evaporated in vacuo at 66° C

Sources & evidence

ORD record
ord-b908d8b76b4f4e52984ba77b0632ecc0
Source dataset
uspto-grants-1996_08
Patent number
US05550149

Reaction notes

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