Potassium Carbonate → 1-(2-Fluorophenyl)piperidine-4-carboxylic acid ethyl ester
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[NH:9]1[CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu](I)I.O>[CH2:16]([O:15][C:13]([CH:12]1[CH2:18][CH2:19][N:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:10][CH2:11]1)=[O:14])[CH3:17]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
1-Fluoro-2-iodobenzene (0.58 mL, 5.0 mmol) was added to a mixture of ethyl isonipecotate (1.2 mL, 7.5 mmol), potassium carbonate (1.4 g, 10 mmol), L-proline (0.12 g, 1 mmol) and copper iodide (0.095 g, 0.5 mmol) in 4 mL of dimethyl sulfoxide. Reaction stirred at 90° C. for 48 hours. The mixture was poured into a water (40 mL) solution and extracted with ethyl acetate (EtOAc) (4×10 mL). The combined organic layers were washed with brine (40 mL) and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo to obtain the crude mixture, which was purified by silica gel flash chromatography, using EtOAc/hexane (gradient system), to obtain 1-(2-fluorophenyl)piperidine-4-carboxylic acid ethyl ester (0.325 g, 26% yield).
Workup
- customReaction
- extractionextracted with ethyl acetate (EtOAc) (4×10 mL)
- washThe combined organic layers were washed with brine (40 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationThe organic layer was concentrated in vacuo
- customto obtain the crude mixture, which
- customwas purified by silica gel flash chromatography
Sources & evidence
- ORD record
- ord-1d1dc6078b3240d1a2586881711ffc03
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07985755B2
Reaction notes
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