tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 178482474, compound
Reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.[CH3:16][NH:17][C:18]1[CH2:22][S:21][C:20](=[O:23])[N:19]=1.CC(C)([O-])C.[K+]>C(O)C>[CH3:16][NH:17][C:18]1=[N:19][C:20](=[O:23])[S:21]/[C:22]/1=[CH:1]\[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
tert-Butyl 4-formylpiperidine-1-carboxylate (1.61 g) and 4-(methylamino)-1,3-thiazol-2(5H)-one (1.18 g) were suspended in ethanol (10 mL), potassium tert-butoxide (1.02 g) was added, and the mixture was stirred at 80° C. for 8 hr. The reaction mixture was concentrated, saturated aqueous ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (1.27 g).
Workup
- concentrationThe reaction mixture was concentrated
- additionsaturated aqueous ammonium chloride solution was added to the residue
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-a2ab593111f2466c8984bed50b0ee5f8
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772277B2
Reaction notes
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