Isobutanol → 1-[4-(4-Isobutoxymethyl-5-phenyl-oxazol-2-yl)-piperidin-1-yl]-ethanone
Reaction equation
[CH2:1]([OH:5])[CH:2]([CH3:4])[CH3:3].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[CH2:17][C:18]1[N:19]=[C:20]([CH:29]2[CH2:34][CH2:33][N:32]([C:35](=[O:37])[CH3:36])[CH2:31][CH2:30]2)[O:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH2:1]([O:5][CH2:17][C:18]1[N:19]=[C:20]([CH:29]2[CH2:34][CH2:33][N:32]([C:35](=[O:37])[CH3:36])[CH2:31][CH2:30]2)[O:21][C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:2]([CH3:4])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
A solution of isobutyl alcohol (0.54 mL, 5.8 mmol) in THF (5 mL) is cooled to 0° C. and treated with sodium bis(trimethylsilyl)amide (5.8 mL of a 1 M solution in THF, 5.8 mmol) and stirred for 1 h. A solution of 1-[4-(4-chloromethyl-5-phenyl-oxazol-2-yl)-piperidin-1-yl]-ethanone (1.69 g, 5.3 mmol), prepared as in Part B, in THF (30 mL) is added dropwise, and the mixture is allowed to warm to 23° C., and stirred for 18 h. The reaction mixture is partitioned between EtOAc (150 mL) and H2O (75 mL), and the organic layer is washed with brine (1×100 mL), dried (MgSO4), and concentrated. The residue is purified by chromatography on silica using EtOAc as eluent to afford the title compound as a yellow oil.
Workup
- stirringstirred for 18 h
- customThe reaction mixture is partitioned between EtOAc (150 mL) and H2O (75 mL)
- washthe organic layer is washed with brine (1×100 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue is purified by chromatography on silica
Sources & evidence
- ORD record
- ord-3b987880633e4993ad607a81bd5c31d5
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090825
Reaction notes
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