Benzylamine → Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate

HRID 654518Notes

Reaction equation

HRID 654518 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]([CH2:4][C:5](OC)=[O:6])=[CH2:3].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:12]([N:19]1[CH2:3][CH:2]([C:1]([O:10][CH3:11])=[O:9])[CH2:4][C:5]1=[O:6])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 69240Dimethyl itaconate

Product 1

HCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of dimethyl itaconate (50 g, 0.32 mole) in methanol (40 ml) was treated with benzylamine (34.6 ml, 0.32 mole) and the mixture heated under reflux for 2.5h. The solution was then concentrated in vacuo and the residue purified by distillation (b.p. 162°-170° C.0.2 mm) to give a pale yellow oil. This solidified on standing to give the title compound (D10) as a beige solid (66.2 g, 89%), m.p. 62°-63° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2.5h
  3. concentrationThe solution was then concentrated in vacuo
  4. distillationthe residue purified by distillation (b.p. 162°-170° C.0.2 mm)
  5. customto give a pale yellow oil

Sources & evidence

ORD record
ord-aa6f0982a35240ff86a2ccfb7c71b079
Source dataset
uspto-grants-1992_07
Patent number
US05132316

Reaction notes

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