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

HRID 1195189Notes

Reaction equation

HRID 1195189 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 2.5 h. The solution was then concentrated in vacuo and the residue purified by distillation (b.p. 162° C.-170° C./0.2 mmHg) to give a pale yellow oil. This solidified on standing to give the title compound (D16) as a beige solid (66.2 g, 89%), m.p. 62° C.-63° C.

Workup

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

Sources & evidence

ORD record
ord-6a63c8b48fa847b583d6741a042fe186
Source dataset
uspto-grants-1992_05
Patent number
US05110828

Reaction notes

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