Diethyl Ether → 3-(1,2-Dihydro-2-naphthalenyl)-1-methylpyrrolidine

HRID 46501Notes

Reaction equation

HRID 46501 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]1[CH:11]1[CH2:15][C:14](=O)[N:13]([CH3:17])[C:12]1=O.C(OCC)C.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]1[CH:11]1[CH2:15][CH2:14][N:13]([CH3:17])[CH2:12]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 203873593-(1,2-Dihydro-2-naphthalenyl)-1-methyl-2,5-pyrrolidinedione

Product 1

HCID 203873673-(1,2-Dihydro-2-naphthalenyl)-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The 3-(1,2-dihydro-2-naphthalenyl)-1-methyl-2,5-pyrrolidinedione, 60 g, is taken up in dioxane and added dropwise to a suspension of 40 g of lithium aluminum anhydride (LAH) in 2 l. diethyl ether. After 5 hours at reflux, the mixture is decomposed with K2CO3 solution and filtered. Evaporation of the organic layer leaves 42.8 g of 3-(1,2-dihydro-2-naphthalenyl)-1-methylpyrrolidine which is distilled at 125°-150°/0.2 mm IR and NMR consistent, 28 g yield (54%).

Workup

  1. temperatureAfter 5 hours at reflux
  2. filtrationfiltered
  3. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-0ffd36cad68a4ccbaa74fbfc5643cc59
Source dataset
uspto-grants-1979_11
Patent number
US04173640

Reaction notes

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