Water → HCID 86671379, compound
Reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[H-].[Na+].CS(O[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)(=O)=O.O>CN(C)C=O>[CH:6]([C:4]1[N:3]=[CH:2][N:1]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH:5]=1)=[O:7]Participants
Conditions
- Temperature
- 0 °C
Procedure
To 137 mg of imidazole-4-carboxaldehyde diluted in 2 ml of anhydrous dimethylformamide under argon are added portionwise at 0° C. 63 mg of sodium hydride (60% in mineral oil). The reaction mixture is stirred for 45 min at 0° C. then 400 mg of tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate are added portionwise, and the solution is brought to 100° C. for 15 h. Water is added and the product is extracted several times with ethyl acetate. The organic phases are combined, washed with sodium chloride saturated aqueous solution, dried over magnesium sulfate, and concentrated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 2:8 to 100% ethyl acetate) to yield 92 mg of tert-butyl 4-(4-formyl-1H-imidazol-1-yl)piperidine-1-carboxylate in the form of a colourless oil.
Workup
- additionare added portionwise at 0° C
- waitthe solution is brought to 100° C. for 15 h
- extractionthe product is extracted several times with ethyl acetate
- washwashed with sodium chloride saturated aqueous solution
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 2:8 to 100% ethyl acetate)
Sources & evidence
- ORD record
- ord-00876b4c90c84ba9b2463c45bf607223
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889711B2
Reaction notes
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