Acetonitrile → (S)-tert-Butyl 2-(4-(2-cyanoacetyl)phenyl)morpholine-4-carboxylate
Reaction equation
C([Li])CCC.CCCCCC.[C:12](#[N:14])[CH3:13].C[O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]2[O:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]2)=[CH:21][CH:20]=1)=O>O1CCCC1>[C:12]([CH2:13][C:17]([C:19]1[CH:20]=[CH:21][C:22]([C@@H:25]2[O:30][CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26]2)=[CH:23][CH:24]=1)=[O:16])#[N:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
n-Butyllithium 1.6 M in hexane (1.63 ml, 2.61 mmol) was diluted with tetrahydrofuran (2 ml) and cooled to −78° C. Acetonitrile (107 mg, 0.137 ml, 2.61 mmol) was added dropwise and stirring was continuing for 1 hour. (S)-tert-butyl 2-(4-(methoxycarbonyl)phenyl)morpholine-4-carboxylate (420 mg, 1.31 mmol) dissolved in tetrahydrofuran was slowly added to the white slurry over a 10 min period. After 3 hours, the reaction was quenched by addition of saturated ammonium chloride solution (5 ml) and extracted with diethyl ether (10 ml). The organic layer was dried over MgSO4 and evaporated.
Workup
- additionwas slowly added to the white slurry over a 10 min period
- waitAfter 3 hours
- customthe reaction was quenched by addition of saturated ammonium chloride solution (5 ml)
- extractionextracted with diethyl ether (10 ml)
- dry with materialThe organic layer was dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-940867ba6b2b4adeb74d2719a0990200
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181230B2
Reaction notes
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