1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine → Tert-butyl 4-(methylthio)piperidine-1-carboxylate

HRID 473802Notes

Reaction equation

HRID 473802 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[CH3:19][S-:20].[Na+]>CO>[CH3:19][S:20][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 4378561Sodium methanethiolate

Product 1

HCID 11053478Tert-butyl 4-(methylthio)piperidine-1-carboxylateYield 58.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (2.0 g, 7.2 mmol) and sodium thiomethoxide (1.0 g, 14.4 mmol) in methanol (30 mL) was refluxed for 15 h and then concentrated. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulfate, filtered and concentrated. Column chromatography on silica (3% ethyl acetate in hexanes) afforded tert-butyl 4-(methylthio)piperidine-1-carboxylate (0.98 g, 58% yield) as a colorless oil. MS (EI) for C11H21NO2S: 231 (M+).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b9542cd363ec4ca29942888476db3072
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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