Water → n-{[(7s)-3, 4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-n-methyl-ethane-1,2-diamine

HRID 657550Notes

Reaction equation

HRID 657550 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][N:14]([CH2:16][C:17]#[N:18])[CH3:15])[CH2:6]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[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]([CH3:15])[CH2:16][CH2:17][NH2:18])[CH2:6]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86628627[{[(7S)-3, 4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]acetonitrile

Product 1

HCID 68533266n-{[(7s)-3, 4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}-n-methyl-ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.1 g (4.5 mmol) of the compound of Step 1 in 10 mL of THF is poured dropwise into 0.21 g (5.4 mmol) lithium aluminium hydride suspended in 5 mL of THF, at ambient temperature, and is then stirred at ambient temperature for 5 hours. Cooling to about 0° C. is carried out and there are then added, cautiously, in succession, 0.14 mL of water, 0.11 mL of 20% aqueous sodium hydroxide solution and 0.51 mL of water. Stirring is carried out overnight at ambient temperature, and then the salts are filtered off over a frit and rinsed with THF. The combined filtrates are concentrated to yield the desired product.

Workup

  1. temperatureCooling to about 0° C.
  2. additionthere are then added
  3. stirringStirring
  4. waitis carried out overnight at ambient temperature
  5. filtrationthe salts are filtered off over a frit
  6. washrinsed with THF
  7. concentrationThe combined filtrates are concentrated

Sources & evidence

ORD record
ord-4c142e41789f4f289c1f0cbaf5dbd007
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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