Sodium Cyanide → tert-Butyl-7-(cyanomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2167439Notes

Reaction equation

HRID 2167439 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18]Br)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-:20]#[N:21].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][C:20]#[N:21])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 669783501158756-43-4

Product 1

HCID 66978184tert-Butyl-7-(cyanomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylateYield 94.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 21.76 mmol of tert-butyl-7-(bromomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate in 80 ml DMF were added at 0° C. 65.3 mmol sodium cyanide in small portions. The mixture was stirred at room temperature for 2 h. Brine solution was added to the mixture and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and filtered. Evaporation of the solvent gave 5.6 g of a brown oil. The material was purified by flash chromatography to yield 1.63 g of a pale yellow solid (27.5%).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-928ad62f5a80477b9c0194d47ca568ac
Source dataset
uspto-grants-2015_06
Patent number
US09045459B2

Reaction notes

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