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

HRID 273990
Notes
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Reaction equation

HRID 273990 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent
2×

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-693d722eac484f8a9dfab0bffad5cf4f
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05387685

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes