Sodium Carbonate → HCID 21543121, compound

HRID 1606498Notes

Reaction equation

HRID 1606498 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:18]=[C:17]3[CH:12]([CH2:13][CH2:14][N:15]([CH3:19])[CH2:16]3)[CH:11]3[C:20](=O)[N:21]([CH3:24])[C:22](=O)[CH:10]23)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH:18]=[C:17]3[CH:12]([CH2:13][CH2:14][N:15]([CH3:19])[CH2:16]3)[CH:11]3[CH2:20][N:21]([CH3:24])[CH2:22][CH:10]23)=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 21226445Aluminium lithium hydrideHCID 21543112HCID 21543112, compound

Product 1

HCID 21543121HCID 21543121, compoundYield 90%

Procedure

A solution of 6.7 g (0.02 moles) of 3a,4,6,7,8,9,9a,9b-octahydro-4-(p-methoxyphenyl)-2,7-dimethyl-2H-pyrrolo[3,4-f]-isoquinoline-1,3-dione in 100 ml of dichloromethane-ether (1:1) is added to a slurry of 3 g (0.08 moles) lithium aluminum hydride in 300 ml dichloromethane-ether (1:1) under nitrogen. This is refluxed for 18 hours. Saturated sodium carbonate solution is added at room temperature until the reaction is white. The salts are filtered and washed with dichloromethane. The combined filtrates are evaporated to yield 5.5 g (90%) 1,3,3a,4,6,7,8,9,9a,9b-decahydro-4-(p-methoxyphenyl)-2,7-dimethyl-2H-pyrrolo[3,4-f]isoquinoline. This is dissolved in isorpopanol-ether, and hydrochloric acid in isopropanol is added until the solution is acidic to pH paper. Excess ether is added and the white solid product is filtered.

Workup

  1. temperatureThis is refluxed for 18 hours
  2. filtrationThe salts are filtered
  3. washwashed with dichloromethane
  4. customThe combined filtrates are evaporated

Sources & evidence

ORD record
ord-f33119b312e44a579c0e7e7aa7f4f44b
Source dataset
uspto-grants-1976_04
Patent number
US03953434

Reaction notes

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