Ethyl chloroacetate → (2,2-Dimethyl-pyrrolidin-1-yl)-acetic acid ethyl ester

HRID 644080

Reaction equation

HRID 644080 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5]Cl)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:14][C:15]1([CH3:20])[CH2:19][CH2:18][CH2:17][NH:16]1>C(O)C.C(OCC)C>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][N:16]1[CH2:17][CH2:18][CH2:19][C:15]1([CH3:20])[CH3:14])[CH3:2]

Participants

6

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 4147732,2-Dimethylpyrrolidine

Product 1

HCID 63219360(2,2-Dimethyl-pyrrolidin-1-yl)-acetic acid ethyl esterYield 61.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethylchloroacetate (0.15 ml, 1.37 mmol), potassium carbonate (416 mg, 1.5 mmol) and 2,2-dimethyl-pyrolidine (0.280 mg, 2.06 mmol) were suspended in ethanol (3 ml) and subjected to microwave irradiation at 120° C. for 45 min. The resultant mixture was suspended in diethyl ether (30 ml), extracted with 2M hydrochloric acid (30 ml) and the organic layer discarded. The aqueous layer was treated with a slight excess of 4N sodium hydroxide solution and extracted with diethyl ether (3×30 ml). The organic layers were combined, dried over sodium sulfate, filtered and solvent removed under reduced pressure to afford (2,2-dimethyl-pyrrolidin-1-yl)-acetic acid ethyl ester (156 mg).

Workup

  1. customirradiation at 120° C. for 45 min
  2. extractionextracted with 2M hydrochloric acid (30 ml)
  3. additionThe aqueous layer was treated with a slight excess of 4N sodium hydroxide solution
  4. extractionextracted with diethyl ether (3×30 ml)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-7bfcbf497a894ea8867f2117c7808ace
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Linked notes

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