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

HRID 2074853
Notes
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Reaction equation

HRID 2074853 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent
HCID 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-dfe98758f79d45268047e7f689880e97
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07919491B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes