Sodium hydride → HCID 68777402, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:18][C:19](=[O:24])[CH2:20][CH2:21][CH2:22]Cl)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4].[H-].[Na+]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1([N:18]2[CH2:22][CH2:21][CH2:20][C:19]2=[O:24])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The ester compound in dry THF (15 mL) was added to a suspension of NaH (352 mgs, 8.81 mmol) in dry THF (3 mL) and stirred at room temperature for 16 hours. The reaction mixture was then quenched with water (4 mL), diluted with ethyl acetate (60 mL), dried over MgSO4, filtered, and purified by flash chromatography on silica gel with stepwise elution using 50% ethyl acetate/hexanes to 100% ethyl acetate/hexanes gave 4-(2-oxo-pyrrolidin-1-yl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (1.28 g, 58.0% yield).