Benzyl chloroformate → Benzyl 3-pyrroline-1-carboxylate

HRID 400449Notes

Reaction equation

HRID 400449 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:19]1[CH2:23][CH:22]=[CH:21][CH2:20]1)C1C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]([N:19]1[CH2:23][CH:22]=[CH:21][CH2:20]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 643471Benzyl 3-pyrroline-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

43 mL benzyloxycarbonyl chloride in 135 mL dichlormethane was added to 17.6 g 1-benzyl-2,5-dihydro-1H-pyrrole in 135 mL dichlormethane at 0° C. in 60 min. The mixture was stirred 3 h at RT and washed with saturated sodium hydrogencarbonate solution. The organic layer was dried and evaporated. The residue was purified by chromatography on silica gel (hexane/ethyl acetate: 5/1) to give 19.7 g of the desired product.

Workup

  1. washwashed with saturated sodium hydrogencarbonate solution
  2. customThe organic layer was dried
  3. customevaporated
  4. customThe residue was purified by chromatography on silica gel (hexane/ethyl acetate: 5/1)

Sources & evidence

ORD record
ord-9046dd2206b54659ba959159c5c333c1
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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