Diisopropylamine → HCID 15084248, compound
Reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19].[C:20](OCC)(=[O:22])[CH3:21]>C1COCC1.CCCCCC>[C:20]([CH:16]1[CH2:17][CH2:18][N:14]([CH3:13])[C:15]1=[O:19])(=[O:22])[CH3:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
20.40 g (0.20 mol) of diisopropylamine were placed in 200 ml dry THF under nitrogen and 80 ml n-butyl lithium in hexane (2.5 M) were added dropwise. It was allowed to stir for 20 minutes and then 20.00 g (0.20 mol) of 1-methyl-2-pyrrolidinone were added dropwise at −78° C. After stirring the reaction mixture for 1 hour 17.64 g (0.20 mol) of dry ethyl acetate were added at −78° C. The reaction mixture was warmed to room temperature and stirred for 14 hours. The THF was removed on a rotary evaporator under reduced pressure and the residue was taken up in 80 ml of 6 N HCl. The acidic aqueous phase was saturated with NaCl and extracted 5 times with 300 ml ethyl acetate. The combined organic layers were dried over Na2SO4, and the solvent was removed on a rotary evaporator. The remaining yellow oil was purified by column chromatography. This gave 5.10 g product as a light yellow oil.
Workup
- additionwere added at −78° C
- stirringstirred for 14 hours
- customThe THF was removed on a rotary evaporator under reduced pressure
- extractionextracted 5 times with 300 ml ethyl acetate
- dry with materialThe combined organic layers were dried over Na2SO4
- customthe solvent was removed on a rotary evaporator
- customThe remaining yellow oil was purified by column chromatography
Sources & evidence
- ORD record
- ord-3014757f2b3f4323ad89c0455a1c0489
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394324B2
Reaction notes
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