Diisopropylamine → HCID 68547099, compound
Reaction equation
C([Li])CCC.C(NC(C)C)(C)C.C[Si](C)(C)[N:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20].[CH:23]1[N:24]=[CH:25][N:26]2[CH2:31][CH2:30][CH2:29][C:28](=[O:32])[C:27]=12>O1CCCC1>[OH:32][C:28]1([CH:17]2[CH2:18][CH2:19][NH:15][C:16]2=[O:20])[CH2:29][CH2:30][CH2:31][N:26]2[CH:25]=[N:24][CH:23]=[C:27]12Participants
Procedure
1.25 ml of n-butyllithium (1.6M in hexane) are added dropwise to a solution to 0.29 ml of diisopropylamine and 2 ml of tetrahydrofuran at −78° C. After 30 minutes, a solution, cooled to −78° C., of 0.31 g of 1-trimethylsilanylpyrrolidin-2-one and 5 ml of tetrahydrofuran is added dropwise. The mixture is stirred for a further 30 minutes and then a solution of 0.27 g of 6,7-dihydro-5H-imidazo[1,5-a]pyridin-8-one [426219-51-4] and 5 ml tetrahydrofuran is added dropwise. The reaction mixture is stirred at −78° C. for 1 hour and then at 0° C. for 2 hours. The mixture is quenched with saturated aqueous ammonium chloride solution/water (1:1), the tetrahydrofuran is evaporated, and the residue is extracted with dichloromethane (3×). The combined organic phases are dried with sodium sulphate and evaporated. The title compound is identified from the residue by flash chromatography (SiO2 60F) on the basis of the Rf.
Workup
- additionis added dropwise
- stirringThe reaction mixture is stirred at −78° C. for 1 hour
- waitat 0° C. for 2 hours
- customThe mixture is quenched with saturated aqueous ammonium chloride solution/water (1:1)
- customthe tetrahydrofuran is evaporated
- extractionthe residue is extracted with dichloromethane (3×)
- dry with materialThe combined organic phases are dried with sodium sulphate
- customevaporated
Sources & evidence
- ORD record
- ord-b5a28f866dd644b983b71d801b45ba84
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07612088B2
Reaction notes
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