Ethyl Acetate → HCID 86685238, compound
Reaction equation
[CH:1]1([C:5]#[N:6])[CH2:4][CH2:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].[O:15]=[C:16]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1.CCOC(C)=O>C1COCC1>[C:5]([C:1]1([C:16]2([OH:15])[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:17]2)[CH2:4][CH2:3][CH2:2]1)#[N:6]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of cyclobutanecarbonitrile (1.75 g, 21.5 mmol) in THF (15 mL) was added 2.0M lithium diisopropylamide (11 mL, 22.5 mmol) dropwise and the solution was stirred at −78° C. for 45 minutes. Then a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (4.0 g, 21.5 mmol) in THF (2 mL) was added to the solution and the mixture was stirred at −78° C. for 2 hours. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOAc (25 mL×3). The organic phase was washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography eluted with petroleum ether:EtOAc=2:1 to obtain the title compound (0.9 g, 38.2% yield) as a white solid. 1H NMR: (400 MHz, CDCl3): δ 3.64-3.40 (m, 4H), 2.44 (t, J=7.8 Hz, 2H), 2.33-2.23 (m, 2H), 2.13-1.88 (m, 4H), 1.47 (s, 9H)
Workup
- stirringthe mixture was stirred at −78° C. for 2 hours
- customThe reaction mixture was quenched with saturated NH4Cl solution
- extractionextracted with EtOAc (25 mL×3)
- washThe organic phase was washed with brine (20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography
- washeluted with petroleum ether
Sources & evidence
- ORD record
- ord-b62ea2b0159148abb5c7e166f6d95e19
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772500B2
Reaction notes
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