Ethyl oxoacetate → Hydroxy-(2-oxo-4-propyl-pyrrolidin-1-yl)-acetic acid ethyl ester
Reaction equation
[CH2:1]([CH:4]1[CH2:8][NH:7][C:6](=[O:9])[CH2:5]1)[CH2:2][CH3:3].[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[O:12]>CC(C)=O>[CH2:15]([O:14][C:10](=[O:13])[CH:11]([OH:12])[N:7]1[CH2:8][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][C:6]1=[O:9])[CH3:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
In a 250 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, a mixture of 4-propyl-pyrrolidin-2-one (0.5 g, 3.9 mmol) and ethyl glyoxylate (50% in toluene, 2.4 ml, 11 mmol) in acetone is heated up at 60° C. for 6 h and another portion of ethyl glyoxylate (0.4 ml) is added. After 17 h at 50° C., the reaction mixture is concentrated in vacuo to give the crude hydroxy-(2-oxo-4-propyl-pyrrolidin-1-yl)-acetic acid ethyl ester a19 (2.02 g). It is used in the next step without any further purification.
Workup
- concentrationthe reaction mixture is concentrated in vacuo
Sources & evidence
- ORD record
- ord-55f9e2752e6a47a8bec4993f652e166c
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07244747B2
Reaction notes
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