Acetic Acid → tert-Butyl 4-{[6-formyl-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate
Reaction equation
[OH:1][CH:2]([C:5]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:8]=[C:7]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH:6]=1)CO.C(O)(=O)C.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.CCOCC>[CH:2]([C:5]1[N:10]=[C:9]([C:11]([F:14])([F:12])[F:13])[N:8]=[C:7]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH:6]=1)=[O:1]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of tert-butyl 4-{[6-(1,2-dihydroxyethyl)-2-(trifluoromethyl)pyrimidin-4-yl]oxy}piperidine-1-carboxylate (542 mg, 1.33 mmol) in THF (10. mL) and water (6.0 mL) was added acetic acid (20. μL, 0.35 mmol) and sodium periodate (854 mg, 3.99 mmol) at −5° C. After stirring for 30 minutes, the reaction mixture was diluted with ether and water. The aqueous layer was extracted with ethyl acetate once and the combined organic layers were washed with brine and dried over anhydrous Na2SO4. The organic solvent was removed in vacuo and the residue was purified with silica gel column to give the desired product as colorless oil. LCMS (M+H)+: 376.1.
Workup
- extractionThe aqueous layer was extracted with ethyl acetate once
- washthe combined organic layers were washed with brine
- dry with materialdried over anhydrous Na2SO4
- customThe organic solvent was removed in vacuo
- customthe residue was purified with silica gel column
Sources & evidence
- ORD record
- ord-ed68d2ea40474febb3d0bec3b40cec7d
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933085B2
Reaction notes
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