Acetic Acid → 1-(5-Fluoropyridin-2-yl)piperidine-4-carboxylic acid
Reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.O[Li].O.C(O)(=O)C.C(OCC)(=O)C>C1COCC1.O.CO>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:9]2[CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)=[N:13][CH:14]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 20 °C
Procedure
A mixture of 4 g (16 mmol) 5′-Fluoro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester and 0.832 g (20 mmol) LiOH.H2O in 50 mL THF, 50 mL water and 5 mL methanol was stirred for 2 h at 20° C. Acetic acid was added to pH 6 and water and ethyl acetate. The mixture was extracted with ethyl acetate and the combined organic layers were washed with brine, dried with Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography on silica eluting with a gradient formed from heptane and ethyl acetate. The product containing fractions were evaporated to yield 3.1 g (87%) of the title compound as off-white solid. MS m/e: 223.1 [M−H].
Workup
- extractionThe mixture was extracted with ethyl acetate
- washthe combined organic layers were washed with brine
- dry with materialdried with Na2SO4
- filtrationfiltered
- customevaporated to dryness
- customThe residue was purified by column chromatography on silica eluting with a gradient
- customformed from heptane and ethyl acetate
- additionThe product containing fractions
- customwere evaporated
Sources & evidence
- ORD record
- ord-44e9136703e540d39c8bdc50d13226f6
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09226916B2
Reaction notes
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