Tetrahydrofuran → tert-Butyl 6-methoxy-2-methyl3-[{2-oxopiperazin-1-yl}acetyl]benzonitrile
Reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C([N-][CH:19]([CH3:21])[CH3:20])(C)C.[Li+].Br[CH2:24][C:25]([C:27]1[C:28]([CH3:37])=[C:29]([C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[C:30]#[N:31])=[O:26].[CH2:38]1COCC1>>[C:19]([C:34]1[CH:33]=[C:32]([O:35][CH3:36])[C:29]([C:30]#[N:31])=[C:28]([CH3:37])[C:27]=1[C:25](=[O:26])[CH2:24][N:7]1[CH2:6][CH2:5][NH:4][CH2:3][C:2]1=[O:1])([CH3:21])([CH3:38])[CH3:20]Participants
5
Procedure
To a THF solution of tert-butyl 3-oxopiperazine-1-carboxylate (0.082 g, 0.41 mmol) was added Lithium diisopropylamide (0.24 mL, 0.39 mmol) dropwise at −78° C. After stirring for 15 minutes, a THF solution of 3-(Bromoacetyl)-6-methoxy-2-methylbenzonitrile (0.10 g, 0.37 mmol) was added to the reaction mixture slowly. Analysis of the reaction mixture by LC indicated formation of the desired product. To the reaction mixture was added saturated NH4Cl, followed by extraction of the aqueous layer with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to provide a residue which was purified by silica gel column chromatography to provide the title product.
Sources & evidence
- ORD record
- ord-9f56e075eedf42a4a1a1063280809d6a
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999990B2
Reaction notes
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