Methyl chloroformate → 1-Methoxycarbonyl-3-pyrroline

HRID 352751Notes

Reaction equation

HRID 352751 reaction equation
[CH2:1]([N:3](CC)[CH2:4][CH3:5])[CH3:2].Cl[C:9]([O:11][CH3:12])=[O:10]>ClCCl.N1CC=CC1>[CH3:12][O:11][C:9]([N:3]1[CH2:4][CH:5]=[CH:2][CH2:1]1)=[O:10]

Participants

5

Reactant 2

HCID 6586Methyl chloroformateHCID 8471Triethylamine

Product 1

HCID 8199331-Methoxycarbonyl-3-pyrroline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 660593-PyrrolineSolvent

Procedure

In dichloromethane (20 ml), 3-pyrroline (1.1 ml) was dissolved, followed by the addition of triethylamine (2.6 ml) and methyl chloroformate (1.2 ml) under ice cooling. The resulting mixture was stirred at room temperature for 17 hours. The residue obtained by distilling the reaction mixture under reduced pressure was purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby the title compound (0.95 g, 52%) was obtained.

Workup

  1. customThe residue obtained
  2. distillationby distilling the reaction mixture under reduced pressure
  3. customwas purified by chromatography on a silica gel column (hexane:ethyl acetate=4:1), whereby the title compound (0.95 g, 52%)
  4. customwas obtained

Sources & evidence

ORD record
ord-b8ad593fc76f47d88051794e520b12c3
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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