Carbon Dioxide → HCID 19980407, compound
Reaction equation
[CH3:1][N:2]([CH2:4][C:5]([CH3:7])=[CH2:6])[CH3:3].C([Li])CCC.C(=O)=O.[CH2:16]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)=[O:20])[CH3:17]>C1COCC1>[CH2:16]([O:18][C:19]([N:21]1[CH2:22][CH2:23][C:24]([OH:27])([CH2:6][C:5]([CH2:4][N:2]([CH3:3])[CH3:1])=[CH2:7])[CH2:25][CH2:26]1)=[O:20])[CH3:17]Participants
Procedure
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)
Workup
- additionthe temperature of addition
- temperaturebeing maintained below 0°
- temperaturethe reaction mixture maintained at 0° for 3 hours
- temperaturecooled to -78°
- temperaturethe reaction mixture maintained at -78° for 1.5 hours
- washthe reaction mixture washed with saturated NaCl several times
- dry with materialdried (MgSO4)
Sources & evidence
- ORD record
- ord-4b4eeec83cdc4a6a8a76ccd4b7765f12
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05075317
Reaction notes
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