Water → Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate
Reaction equation
[OH:1][CH2:2][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.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>O1CCCC1>[CH3:23][S:24]([O:1][CH2:2][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:26])=[O:25]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
t-butyl 4-Hydroxymethyl-1-piperidinecarboxylate (5.00 g, 23.2 mmol) was dissolved in tetrahydrofuran (75 ml). To the solution were added triethylamine (2.83 g) and methanesulfonyl chloride (3.19 g) under ice cooling, and the mixture was stirred at 0° C. for 5 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with 1N-hydrochloric acid and a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid materials were washed with hexane to give the titled compound (6.55 g, 22.3 mmol, Yield 96%).
Workup
- extractionthe mixture was extracted with ethyl acetate twice
- washThe organic layer was washed with 1N-hydrochloric acid
- dry with materiala saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- washThe resulting solid materials were washed with hexane
Sources & evidence
- ORD record
- ord-c479885c803f4422b7282852f92998d7
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562978B1
Reaction notes
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