Carbon Dioxide → HCID 19980407, compound

Participants

Reaction Steps

2-[(Dimethylamino)methyl]propene (29.75 g, 300 mmol) in anhydrous THF (300 ml) was cooled to -78° and butyl lithium (2.5M, 120 ml, 300 mmol) was added dropwise, the temperature of addition being maintained below 0°. The dry-ice bath was replaced by an ice-bath and the reaction mixture maintained at 0° for 3 hours and then cooled to -78°. 1-Ethoxycarbonyl-4-piperidinone (25.68 g, 150 mmol) in anhydrous THF (50 ml) was added dropwise and the reaction mixture maintained at -78° for 1.5 hours and then stirred at room temperature overnight. Approximately 50 g of ice was added and the reaction mixture washed with saturated NaCl several times and dried (MgSO4), yielding a tan, viscous oil (42.47 g). Purification by flash chromatography eluting with ethylacetate in hexane gave the sub-title compound (9.33 g)

Provenance & Evidence