Ethyl Acetate → Diethyl 1-(bromoacetyl)-2,2-pyrrolidinedicarboxylate

HRID 421206Notes

Reaction equation

HRID 421206 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].[Br:22][CH2:23][C:24](Br)=[O:25].C(OCC)(=O)C>ClCCl.O>[Br:22][CH2:23][C:24]([N:1]1[CH2:5][CH2:4][CH2:3][C:2]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:25]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 12524347Diethyl 2,2-pyrrolidinedicarboxylate

Product 1

HCID 59215802Diethyl 1-(bromoacetyl)-2,2-pyrrolidinedicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of diethyl 2,2-pyrrolidinedicarboxylate (D63, 900 mg) in dichloromethane (9 mL) at 0° C., potassium carbonate (0.5M solution, 12.5 mL) and bromoacetyl bromide (0.55 mL) were added. The resulting mixture was stirred at 0° C. for 2 hours. The mixture was then diluted with water and then allowed to reach r.t. Ethyl acetate (15 mL) was added and phases were separated. The aqueous phase was then extracted with ethyl acetate (2×10 mL) and washed with brine (20 mL). The organic phase was dried and concentrated in vacuo to give the desired compound (1.06 g) as orange oil.

Workup

  1. customto reach r.t
  2. customphases were separated
  3. extractionThe aqueous phase was then extracted with ethyl acetate (2×10 mL)
  4. washwashed with brine (20 mL)
  5. customThe organic phase was dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18773e2065f3476d8a70f05a272ab7d8
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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