Water → tert-Butyl 3-(tosyloxy)piperidine-1-carboxylate

HRID 1012285Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:1][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (2.00 g, 9.94 mmol) in chloroform (20 ml) were successively added p-toluenesulfonyl chloride (2.27 g, 11.9 mmol) and triethylamine (1.66 ml, 11.9 mmol) at 0° C., and the mixture was stirred at 70° C. for 9 hr. The reaction mixture was allowed to cool to room temperature, water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was successively washed with water and saturated brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:hexane=1:1) to give tert-butyl 3-(toluene-4-sulfonyloxy)piperidine-1-carboxylate (1.00 g, yield 28%).

Workup

customat 0° C.
temperatureto cool to room temperature
extractionthe mixture was extracted with chloroform
washThe organic layer was successively washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter filtration
concentrationthe solvent was concentrated under reduced pressure
customthe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record: ord-df199b96dc60464aa19642e23f0ecc61
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977331B1

Reaction notes

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