Water → HCID 13281975, compound

HRID 904759Notes

Reaction equation

HRID 904759 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:18][CH2:17][CH2:16][CH:15]=[C:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH:23]1([CH2:26]CS([O-])(=O)=O)[CH2:25][CH2:24]1.O>CN(C)C=O>[CH:23]1([CH2:26][N:12]2[C:11](=[O:20])[CH2:10][C:9]3([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)[C:14](=[CH:15][CH2:16][CH2:17][CH2:18]3)[C:13]2=[O:19])[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 132819714a-(m-Methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinolineHCID 53436356HCID 53436356, compound

Product 1

HCID 13281975HCID 13281975, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4a-(m-Methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6, 7-octahydroisoquinoline (99 g, 0.365 moles) in 1000 ml of anhydrous dimethylformamide was added dropwise to a 55% suspension of sodium hydride in mineral oil (19.8 g) in 500 ml of dimethylformamide at 70°. The reaction mixture was heated for 1 hour at 80° and then cooled to 25°. Cyclopropylmethylmesylate (59.6 g) was added and the reaction mixture heated at 70°-80° for one hour and stirred overnight. It was poured into water and extracted with ether. The residue after evaporation of the ether was chromatographed on 800 g of Florisil. The final product, after evaporative distillation at 190° (1μ), amounted to 50 g.

Workup

  1. temperatureThe reaction mixture was heated for 1 hour at 80°
  2. temperaturecooled to 25°
  3. temperaturethe reaction mixture heated at 70°-80° for one hour
  4. extractionextracted with ether
  5. customThe residue after evaporation of the ether
  6. customwas chromatographed on 800 g of Florisil
  7. distillationThe final product, after evaporative distillation at 190° (1μ)

Sources & evidence

ORD record
ord-e6f1945fd2954af0a20860ecd43ad0c5
Source dataset
uspto-grants-1983_12
Patent number
US04419517

Reaction notes

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