Ethyl cyanoformate → HCID 58075576, compound
Reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[N:8]=[CH:7][C:6]([CH:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])=[CH:5][CH:4]=1.[Li+].CC([N-]C(C)C)C.[C:25](C#N)(=[O:29])[O:26][CH2:27][CH3:28]>>[O:14]=[C:10]1[CH:9]([C:6]2[CH:7]=[N:8][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:4][CH:5]=2)[CH2:13][CH2:12][CH:11]1[C:25]([O:26][CH2:27][CH3:28])=[O:29]Participants
4
Conditions
- Temperature
- -78 °C
Procedure
2-(6-(trifluoromethyl)pyridin-3-yl)cyclopentanone (700 mg, 3.05 mmol) was added to a solution of LDA (2.291 mL, 4.58 mmol) at −78° C. After stirring for 30 min at −78° C., ethyl carbonocyanidate (0.329 mL, 3.36 mmol) was added to the reaction mixture. The resulting solution was warmed to room temperature with stirring over 3 h. The reaction mixture was quenched with 1 mL of water, washed with brine, dried over MgSO4, and purified by Biotage (Hexanes/EtOAc 2:1) to afford ethyl 2-oxo-3-(6-(trifluoromethyl)pyridin-3-yl)cyclopentanecarboxylate (764 mg, 2.54 mmol, 83% yield). LC-MS (M+H)+=302.2.
Workup
- temperatureThe resulting solution was warmed to room temperature
- stirringwith stirring over 3 h
- customThe reaction mixture was quenched with 1 mL of water
- washwashed with brine
- dry with materialdried over MgSO4
- custompurified by Biotage (Hexanes/EtOAc 2:1)
Sources & evidence
- ORD record
- ord-cdb61061cdb7443e97661018e5960ec2
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710061B2
Reaction notes
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