Water → N-Cyclopropylmethyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

HRID 26475Notes

Reaction equation

HRID 26475 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@:9]23[CH2:18][CH2:17][CH2:16][CH2:15][C@H: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]Br)[CH2:25][CH2:24]1.O>CN(C)C=O.C1C=CC=CC=1>[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@H:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)[C:13]2=[O:19])[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 867364784a-(m-Methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

Product 1

HCID 86736477N-Cyclopropylmethyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 2.0 g (7.3 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline (Ex. 7A) in 50 ml of anhydrous dimethylformamide was added to 35.1 mg of a 55% suspension of sodium hydride in mineral oil in 25 ml of dimethylformamide heated at 70°. Heating was continued for 45 minutes after the addition was complete after which time 1.09 g (8.1 mmoles) of cyclopropylmethyl bromide in 10 ml of dimethylformamide was added. The reaction mixture was heated at 80° for 2 hours and allowed to stand at 25° overnight. It was poured into water and extracted with ether. Evaporation of the ether gave an oil which showed one spot by thin-layer chromatography (silica gel plates, benzene solvent, Rf 0.4, starting material had Rf 0.07) and was identified by nmr as N-cyclopropylmethyl-4a(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline.

Workup

  1. temperatureheated at 70°
  2. temperatureHeating
  3. additionafter the addition
  4. additionwas added
  5. temperatureThe reaction mixture was heated at 80° for 2 hours
  6. waitto stand at 25° overnight
  7. extractionextracted with ether
  8. customEvaporation of the ether
  9. customgave an oil which

Sources & evidence

ORD record
ord-7519975709794d528196bb799915a4d6
Source dataset
uspto-grants-1979_04
Patent number
US04150135

Reaction notes

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