Trimethylsilyl cyanide → HCID 22175979, compound

HRID 1797746Notes

Reaction equation

HRID 1797746 reaction equation
CS(O[CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:11]([CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:10]2[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=O)=O.C[Si]([C:41]#[N:42])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C.O1CCCC1>[C:27]([O:26][C:24](=[O:25])[NH:23][CH2:22][C:11]1[N:12]([CH2:18][CH:19]([CH3:20])[CH3:21])[C:13](=[O:17])[C:14]2[C:9]([C:10]=1[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[CH:8][C:7]([CH2:6][C:41]#[N:42])=[CH:16][CH:15]=2)([CH3:28])([CH3:29])[CH3:30]

Participants

6

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 22176330HCID 22176330, compound

Product 1

HCID 22175979HCID 22175979, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-4-phenyl-1,2-dihydroisoquinolin-6-yl)methyl methanesulfonate (39 g, 0.75 mmol) in acetonitrile (5 mL) and tetrahydrofuran (4 mL) were added trimethylsilyl cyanide (0.15 mL, 1.1 mmol) and a solution of 1.0 M tetrabutylammonium fluoride: in tetrahydrofuran (1.1 mL), and then the mixture was stirred at 80° C. for 30 min. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2 (v/v)) to give tert-butyl[6-(cyanomethyl)-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl]methylcarbamate (0.25 g, 75%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:2 (v/v))

Sources & evidence

ORD record
ord-9b75ff819eeb45868d91ae56656110f6
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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