HCID 54389077, compound → HCID 53754019, compound

HRID 1076883Notes

Reaction equation

HRID 1076883 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]([C:19]#[N:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:7][C:8](OCC)=[O:9])[CH3:2].[H][H]>[Ni].CO>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][C:8](=[O:9])[NH:20][CH2:19]1)[CH3:2]

Participants

5

Reactant 2

HCID 54389077HCID 54389077, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53754019HCID 53754019, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

45 g of Raney nickel are added to 254.2 g of 3-cyano-3-phenylglutaric acid diethyl ester in 1.5 liters of absolute methanol, and hydrogenation is effected in a 5 liter autoclave for 30 hours at 80° and a hydrogen pressure of 81 atmospheres. After cooling, the catalyst is filtered off, the filtrate is concentrated on a rotary evaporator, the resulting light yellow oil is taken up in 1.5 liters of chloroform and is successively washed with 25 cc of 2 N hydrochloric acid, 100 cc of saturated sodium bicarbonate solution and 100 cc of water. The 5-oxo-3-phenyl-3-pyrrolidine acetic acid ethyl ester, obtained after concentrating the chloroform phase, crystallizes upon triturating with ether. M.P. 49°-51° (from ethyl acetate/petroleum ether).

Workup

  1. temperatureAfter cooling
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated on a rotary evaporator
  4. washis successively washed with 25 cc of 2 N hydrochloric acid, 100 cc of saturated sodium bicarbonate solution and 100 cc of water

Sources & evidence

ORD record
ord-e2bc966bfa214f18ac38a140a27212d2
Source dataset
uspto-grants-1976_05
Patent number
US03958003

Reaction notes

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