Benzyl chloroformate → Benzyl 3-pyrroline-1-carboxylate

HRID 639135Notes

Reaction equation

HRID 639135 reaction equation
[NH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1.Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]>C(Cl)Cl>[N:1]1([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 660593-Pyrroline

Product 1

HCID 643471Benzyl 3-pyrroline-1-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-dihydro-1H-pyrrole (3.3 mL, 43.4 mmol) and Et N (9 mL, 65.1 mmol) in DCM (200 mL) at 0° C. was added dropwise benzyl chloroformate (7.3 mL, 52 mmol). After 1 h, the solution was partitioned between H O-DCM. The organic phase was back extracted several times with DCM and the combined organic fractions were dried (Na SO), concentrated and purified via column chromatography (silica, DCM) yielding the title compound (6 g, 68%) as a yellow oil: LCMS ES (m/e) 204 (M+H).

Workup

  1. customthe solution was partitioned between H O-DCM
  2. customthe combined organic fractions were dried (Na SO)
  3. concentrationconcentrated
  4. custompurified via column chromatography (silica, DCM)

Sources & evidence

ORD record
ord-590d0c1915814f3c9395a9a46f41beb7
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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