Pentane → N-(2-Furylethyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

HRID 26480Notes

Reaction equation

HRID 26480 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+].CCCCC.S(O[CH2:33][CH2:34][C:35]1[O:36][CH:37]=[CH:38][CH:39]=1)(=O)(=O)C>CN(C)C=O>[O:36]1[CH:37]=[CH:38][CH:39]=[C:35]1[CH2:34][CH2:33][N:12]1[C:11](=[O:20])[CH2:10][C@@:9]2([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C@H:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[C:13]1=[O:19]

Participants

6

Reactant 4

HCID 8003PentaneHCID 24758Sodium hydrideHCID 14655779Methanesulfonic acid 2-furan-2-yl-ethyl esterHCID 867364784a-(m-Methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

Product 1

HCID 86736481N-(2-Furylethyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 5.0 g (18.5 mmoles) of 4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline in 100 ml of anhydrous dimethylformamide was added to a stirred suspension of 1.4 g (28 mmoles) of 50% sodium hydride in mineral oil (washed with pentane) in 75 ml of anhydrous dimethylformamide heated at 50° under nitrogen. The mixture was heated at 90° for 2 hours, then cooled to 35°. A solution of 7.1 g (37 mmoles) of freshly prepared 2-furylethyl mesylate (prepared according ot the procedure of Crossland and Servis, J. Org. Chem., 35, 3195 (1970)) in 10 ml of anhydrous dimethylformamide was added and the reaction mixture heated at 90° overnight. It was the cooled and poured into ice-water, and extracted with ether. Evaporation of the ether gave an oil which was purified by column chromatography (Silicar CC-7, eluting with acetone-benzene). The major fraction was identified as N-(2-furylethyl)-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Workup

  1. temperatureheated at 50° under nitrogen
  2. temperatureThe mixture was heated at 90° for 2 hours
  3. temperaturecooled to 35°
  4. temperaturethe reaction mixture heated at 90° overnight
  5. temperaturecooled
  6. extractionextracted with ether
  7. customEvaporation of the ether
  8. customgave an oil which
  9. customwas purified by column chromatography (Silicar CC-7, eluting with acetone-benzene)

Sources & evidence

ORD record
ord-add3d012e6f141daa579f8f76fd05db3
Source dataset
uspto-grants-1979_04
Patent number
US04150135

Reaction notes

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