Sodium Carbonate → [{[(7S)-3, 4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]acetonitrile

HRID 657549Notes

Reaction equation

HRID 657549 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH:14][CH3:15])[CH2:6]2.Br[CH2:17][C:18]#[N:19].C(=O)([O-])[O-].[Na+].[Na+]>C(C(C)=O)C(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][N:14]([CH2:17][C:18]#[N:19])[CH3:15])[CH2:6]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 11534BromoacetonitrileHCID 11499437(S)-1-(3,4-Dimethoxybicyclo(4.2.0)octa-1,3,5-trien-7-yl)-N-methylmethanamine

Product 1

HCID 86628627[{[(7S)-3, 4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]acetonitrile

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

At ambient temperature, 1.04 g (5 mmol) of {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}methylamine, 0.35 mL (5 mmol/1 eq.) of bromoacetonitrile and 2.16 g (20 mmol/4 eq.) of sodium carbonate are mixed into 16 mL of methyl isobutyl ketone. Refluxing is carried out overnight, followed by drying. The residue is taken up in water and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over magnesium sulphate to yield, after concentration, the expected product.

Workup

  1. temperatureRefluxing
  2. customby drying
  3. extractionthe aqueous phase is extracted with dichloromethane
  4. dry with materialThe combined organic phases are dried over magnesium sulphate
  5. customto yield
  6. concentrationafter concentration

Sources & evidence

ORD record
ord-75c30725b881471e9438dcbf42671cea
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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