Trifluoroacetic acid → 4-(6-(Trifluoromethyl)pyridin-2-yl)piperidin-4-ol
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([OH:24])([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:23][C:20]([F:21])([F:22])[C:16]1[N:15]=[C:14]([C:11]2([OH:24])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:19]=[CH:18][CH:17]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 4′-hydroxy-6-trifluoromethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (450 mg, 1.30 mmol) in methylene chloride (5 mL) was treated with trifluoroacetic acid (5 mL). The reaction was stirred at 25° C. for 30 min. At this time, the reaction was concentrated in vacuo to give yellow oil. The oil was dissolved in methylene chloride, washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 6-trifluoromethyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol (320 mg, 100%) as a yellow oil; LRMS for C11H13F3N2O3 (M+H)+ at m/z=246. The NMR spectrum obtained on the sample is compatible with its structure.
Workup
- concentrationAt this time, the reaction was concentrated in vacuo
- customto give yellow oil
- washwashed with a saturated aqueous sodium bicarbonate solution
- dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a8aa36fe9fd44805b60216e6c8ebdff6
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947692B2
Reaction notes
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