Sodium Iodide → Tert-butyl 3-(iodomethyl)piperidine-1-carboxylate
Reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)(=O)=O.[I-:20].[Na+]>CC(C)=O>[I:20][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 58 °C
Procedure
t-Butyl 3-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (Preparation 68, 609.22 g, 2.08 mol, 1 eq) was dissolved in acetone (3 L), and the reaction mixture was flushed with nitrogen. Sodium iodide (619.84 g, 4.16 mol, 2 eq) was added, and the reaction was stirred at reflux (58° C.) under nitrogen. The reaction mixture was cooled to room temperature, filtered, and the solvent removed under vacuum. The residue was re-dissolved in diethyl ether (1.5 L), and this solution was washed with water (500 mL), saturated sodium bicarbonate (400 mL), 5% sodium thiosulfate (400 mL), and brine (400 mL). The solution was dried over sodium sulfate, and the solvent removed under vacuum to afford title compound as a yellow oil (616 g, 1.89 mol, 91%).
Workup
- customthe reaction mixture was flushed with nitrogen
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered
- customthe solvent removed under vacuum
- dissolutionThe residue was re-dissolved in diethyl ether (1.5 L)
- washthis solution was washed with water (500 mL), saturated sodium bicarbonate (400 mL), 5% sodium thiosulfate (400 mL), and brine (400 mL)
- dry with materialThe solution was dried over sodium sulfate
- customthe solvent removed under vacuum
Sources & evidence
- ORD record
- ord-f90497e3130a47fb8886aa03d028f216
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741934B2
Reaction notes
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