Methyl iodide → (4aS,8aS)-4a-(3-Methoxyphenyl)-2-methyloctahydroisoquinolin-6(2H)-one

HRID 1155369Notes

Reaction equation

HRID 1155369 reaction equation
C(N(CC)CC)C.CI.C1O[C:13]2([CH2:22][CH2:21][C@H:20]3[C@:15]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=4)([CH2:16][CH2:17][N:18]([CH3:23])[CH2:19]3)[CH2:14]2)[O:12]C1.O1CCOCC1>CO>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([C@@:15]23[CH2:14][C:13](=[O:12])[CH2:22][CH2:21][C@@H:20]2[CH2:19][N:18]([CH3:23])[CH2:17][CH2:16]3)[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 86738110HCID 86738110, compound

Product 1

HCID 71394941(4aS,8aS)-4a-(3-Methoxyphenyl)-2-methyloctahydroisoquinolin-6(2H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

25.93 g (0.1 mol) of octahydro-4a-(3-methoxyphenyl)-cis-6(2H)-isoquinolinone (see Example 1), 100 ml of benzene, 11.2 ml (0.2 mol) of ethylene glycol and 8.1 ml (125 mmol) of methanesulphonic acid are boiled for 3 hours in a water separator. The mixture is cooled, made basic with aqueous ammonia and extracted with methylene chloride. The organic phase is evaporated to dryness to yield octahydro-4a-(3-methoxyphenyl)-cis-6(2H)-isoquinolinone ethylene ketal. The ketal is dissolved in 50 ml of absolute methanol, cooled to 0° C., and 13.91 ml (0.1 mol) of triethylamine and 7.46 ml (0.12 mol) of methyl iodide are added thereto. The mixture is kept at 22° for 1 hour. The mixture, containing octahydro-4a-(3-methoxyphenyl)-2-methyl-cis-6(2H)-isoquinolinone ethylene ketal, is mixed with 20 ml of dioxane and concentrated by evaporation. 100 ml of dioxane and 100 ml of 2 N aqueous hydrochloric acid are added to the residual oil. The resultant mixture is stirred for 2 hours at 40°, made basic with aqueous ammonia, and extracted with toluene. The extracts are concentrated by evaporation to yield the title compound as an oil, which is crystallized as the hydrogen fumarate from ethanol.

Workup

  1. concentrationconcentrated by evaporation
  2. addition100 ml of dioxane and 100 ml of 2 N aqueous hydrochloric acid are added to the residual oil
  3. extractionextracted with toluene
  4. concentrationThe extracts are concentrated by evaporation

Sources & evidence

ORD record
ord-57d19837aefc4dc78001928a6e79f813
Source dataset
uspto-grants-1981_11
Patent number
US04301290

Reaction notes

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