Pyrrolidine → 1-(1,3-Dioxobutyl)pyrrolidine

HRID 2849

Reaction equation

HRID 2849 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.CC(C)=O.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>C1(C)C=CC=CC=1>[O:6]=[C:2]([CH3:1])[CH2:3][C:4]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:5]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 87118046Diketene acetone

Product 1

HCID 1007221-(1,3-Dioxobutyl)pyrrolidineYield 97.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9 ml (0.05 mol) of diketene-acetone adduct and a solution of 4.2 ml (0.05 mol) of pyrrolidine in 20 ml of toluene were treated as described in preparation 7. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→1%) yielding 7.6 g of the title compound as a dark oil.

Workup

  1. customas described in preparation 7
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→1%)

Sources & evidence

ORD record
ord-fc50405695d1443a80eda06a3dd99d45
Source dataset
uspto-grants-1998_03
Patent number
US05731322

Linked notes

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