Water → 1-Methoxy4-azatricyclo[5,2.2.02,6]undec-8-ene

HRID 1603212Notes

Reaction equation

HRID 1603212 reaction equation
[CH3:1][O:2][C:3]12[CH2:13][CH2:12][CH:9]([CH:10]=[CH:11]1)[CH:8]1[CH:4]2[C:5](=O)[NH:6][C:7]1=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[K+]>O1CCCC1>[CH3:1][O:2][C:3]12[CH2:13][CH2:12][CH:9]([CH:10]=[CH:11]1)[CH:8]1[CH:4]2[CH2:5][NH:6][CH2:7]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 152891533a,4,7,7a-Tetrahydro-4-methoxy-4,7-ethano-1H-isoindole-1,3(2H)-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 152891541-Methoxy4-azatricyclo[5,2.2.02,6]undec-8-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

20.5 g (0.1 mol) of 1-methoxy-4-azatricyclo[5.2.2.02,6 ]undec-8-ene-3,5-dione in 100 ml of absolute tetrahydrofuran are added dropwise to 6 g of LiAlH4 in 200 ml of absolute tetrahydrofuran and the mixture is stirred under reflux overniight. 6 ml each of water, 15% strength KOH solution and water again are added, the inorganic salts are filtered off with suction and boiled out twice with tetrahydrofuran, the filtrates are concentrated and the residue is distilled.

Workup

  1. temperatureunder reflux overniight
  2. filtrationthe inorganic salts are filtered off with suction
  3. concentrationthe filtrates are concentrated
  4. distillationthe residue is distilled

Sources & evidence

ORD record
ord-163f52aae9f64b71a5bbf1e505cb901d
Source dataset
uspto-grants-1999_11
Patent number
US05986105

Reaction notes

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