Tert-butyl 4-cyano-4-(pyridin-2-YL)piperidine-1-carboxylate → 4-(Pyridin-2-yl)piperidine-4-carbonitrile
Reaction equation
[C:1]([C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1)#[N:2]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:3]1([C:1]#[N:2])[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
tert-Butyl 4-cyano-4-pyridin-2-ylpiperidine-1-carboxylate (I-2) (5.45 g, 19 mmole) was dissolved in TFA-DCM (1:1, 50 mL) at 0° C. The resultant reaction mixture was stirred for 40 min at 0° C. After this time, LCMS indicated that the reaction was completion. The reaction mixture solution was concentrated. The residue was treated with 2N NaOH-brine (1: 1, 80 mL) and extracted with EtOAc (5×200 mL). The combined EtOAc extracts were washed with brine, dried over MgSO4, filtered, concentrated to afford the desired product 4-pyridin-2-ylpiperidine4-carbonitrile (I-3) as a yellow solid. Analytical LCMS: single peak (214 nm), 0.962 min. This product was used in next step without further purification.
Workup
- customThe resultant reaction mixture
- concentrationThe reaction mixture solution was concentrated
- additionThe residue was treated with 2N NaOH-brine (1: 1, 80 mL)
- extractionextracted with EtOAc (5×200 mL)
- washThe combined EtOAc extracts were washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4e29ff06eecf4fcfb2f175d908055e14
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07825135B2
Reaction notes
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