Water → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine
Reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>ClCCl>[CH3:22][S:23]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)(=[O:25])=[O:24]Participants
Procedure
(Step 1) tert-Butyl 4-hydroxypiperidine-1-carboxylate (2.5 g, 12 mmol) and triethylamine (2.1 mL, 15 mmol) were dissolved in dichloromethane (30 mL). To the solution was added a solution of methanesulfonyl chloride (1.2 mL, 15 mmol) in dichloromethane (10 mL), followed by stirring for 4 hours, while the temperature was raised to room temperature. To the reaction mixture was added water (50 mL), and the mixture was stirred for 30 minutes, followed by liquid separation. The organic layer was washed successively with 0.50 mol/L hydrochloric acid (40 mL×2) and a saturated aqueous solution of sodium hydrogencarbonate (10 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. To the resulting residue was added a mixed solvent of ethyl acetate and hexane (15 mL, ethyl acetate/hexane=1/2), and the precipitated solid was filtered to obtain tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (3.1 g, 90%).
Workup
- stirringthe mixture was stirred for 30 minutes
- customfollowed by liquid separation
- washThe organic layer was washed successively with 0.50 mol/L hydrochloric acid (40 mL×2)
- dry with materiala saturated aqueous solution of sodium hydrogencarbonate (10 mL), dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- additionTo the resulting residue was added a mixed solvent of ethyl acetate and hexane (15 mL, ethyl acetate/hexane=1/2)
- filtrationthe precipitated solid was filtered
Sources & evidence
- ORD record
- ord-92efe0d6d048451c9ef9eec971e7f50f
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538224B2
Reaction notes
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