Sodium Methoxide → N-Methyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

HRID 26473Notes

Reaction equation

HRID 26473 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[CH2:10][C@@:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3]1=[O:21].C[O-].[Na+]>CO>[CH3:1][N:2]1[C:11](=[O:12])[CH2:10][C@@:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3]1=[O:21]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86736474N-methyl-4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline

Product 1

HCID 86736473N-Methyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-methyl-4a-(m-methoxyphenyl)-1,3-diketo-trans-decahydroisoquinoline (4.6 g, 1.6 mmole) and sodium methoxide (1.84 g, 3.4 mmole) in 150 ml of methanol was stirred at room temperature under nitrogen for 20 hours. It was poured into 150 ml of ice-water and extracted with ether, and the combined extracts were washed with 3 N hydrochloric acid and sat. sodium bicarbonate, dried (Na2SO4) and evaporated. The crude product was a white viscous oil (3.8 g). Thin layer chromatography on silica gel, eluting with 10% ether/benzene, showed a major spot (Rf 0.31) and a minor component (Rf 0.07). The major component, N-methyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline, was clearly separated by preparative thick layer chromatography and isolated as a colorless oil.

Workup

  1. extractionextracted with ether
  2. washthe combined extracts were washed with 3 N hydrochloric acid and sat. sodium bicarbonate
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. washThin layer chromatography on silica gel, eluting with 10% ether/benzene
  6. customThe major component, N-methyl-4a-(m-methoxyphenyl)-1,3-diketo-cis-decahydroisoquinoline, was clearly separated by preparative thick layer chromatography
  7. customisolated as a colorless oil

Sources & evidence

ORD record
ord-b6d4400afbe24cfabbeebb67a6633846
Source dataset
uspto-grants-1979_04
Patent number
US04150135

Reaction notes

Loading…