1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → tert-Butyl 4-(acetylthio)piperidine-1-carboxylate

HRID 379933

Reaction equation

HRID 379933 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]([O-:22])(=[S:21])[CH3:20].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:19]([S:21][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]1)(=[O:22])[CH3:20]

Participants

5

Reactant 2

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 23670855Potassium ethanethioate

Product 1

HCID 22494773tert-Butyl 4-(acetylthio)piperidine-1-carboxylateYield 905.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

In 40 ml of dimethylformamide were dissolved 4.12 g (14.7 mmol) of 1-(tert-butoxycarbonyl)-4-(methanesulfonyloxy)piperidine, and 2.53 g (2.21 mmol) of potassium thioacetate were added to the solution, followed by stirring of the resulting mixture at 105° C. for 4 hours under nitrogen atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate and washed with water and then a saturated aqueous NaCl solution, followed by evaporation of the solvent. The thus obtained residue was subjected to silica gel column chromatography and the fractions eluted with a mixed solvent of hexane-ethyl acetate (5:1) were collected to obtain 5.19 g (yield: 81%) of the title compound as an oil.

Workup

  1. additionwere added to the solution
  2. temperatureAfter cooling
  3. washwashed with water
  4. customa saturated aqueous NaCl solution, followed by evaporation of the solvent
  5. washthe fractions eluted with a mixed solvent of hexane-ethyl acetate (5:1)
  6. customwere collected

Sources & evidence

ORD record
ord-bffff60e8d2d40cca11441a4679f6732
Source dataset
uspto-grants-2001_10
Patent number
US06300357B1

Linked notes

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