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

HRID 1709862Notes

Reaction equation

HRID 1709862 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]([CH2:6][C:7](OC)=[O:8])=[CH2:5].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH3:1][O:2][C:3]([CH:4]1[CH2:6][C:7](=[O:8])[N:19]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:5]1)=[O:11]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 69240Dimethyl itaconate

Product 1

HCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 158.2 g (1.0 mole) of dimethylitaconate and 107.2 g (1.0 mole) of benzylamine in 750 ml of methanol was let stand at ambient temperature over the weekend. The solution was filtered and the filtrate was concentrated under reduced pressure to give an oil as residue. The oil crystallized when it was triturated with petroleum ether (30°-60° C.). The solid was collected by filtration and dried to yield 225.5 g (97%) of the title compound as a white powder. An analytical sample, m.p. 63°-65° C., was prepared from 2-propyl ether.

Workup

  1. customwas let stand at ambient temperature over the weekend
  2. filtrationThe solution was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto give an oil as residue
  5. customThe oil crystallized when it
  6. customwas triturated with petroleum ether (30°-60° C.)
  7. filtrationThe solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-3014d43c31cc4b83b007521f44d5ddf2
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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