Sodium Iodide → tert-Butyl 3-iodopiperidine-1-carboxylate

HRID 1643463Notes

Reaction equation

HRID 1643463 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)(=O)=O.[I-:19].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O>[I:19][CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 568122N-Boc-3-mesyloxypiperidine

Product 1

HCID 21580769tert-Butyl 3-iodopiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

tert-Butyl 3-(methylsulfonyloxy)piperidine-1-carboxylate (0.54 g, 1.94 mmol) and sodium iodide (0.87 g, 5.8 mmol) were dissolved in acetone (10 ml) and the solution was refluxed under an inert gas for 6 h and then stirred at room temperature for 15 h. After thin layer chromatography control, the reaction mixture was heated in three portions in a microwave oven (CEM Discover): 10 min 100° C. 150 watt, 15 min 150° C. 200 watt, 20 min 100° C. 150 watt. After thin layer chromatography control, the three portions were combined, sodium thiosulfate solution (20 ml, 5 mmol/l) was added, the phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phases were washed with saturated sodium chloride solution (10 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (3:1). Yield: 0.14 g (23%)

Workup

  1. temperaturethe solution was refluxed under an inert gas for 6 h
  2. temperatureAfter thin layer chromatography control, the reaction mixture was heated in three portions in a microwave oven (CEM Discover)
  3. custom10 min 100° C
  4. custom150 watt, 15 min 150° C
  5. custom200 watt, 20 min 100° C
  6. customthe phases were separated
  7. extractionthe aqueous phase was extracted with ethyl acetate (2×20 ml)
  8. washThe combined organic phases were washed with saturated sodium chloride solution (10 ml)
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by column chromatography (silica gel) with hexane/diethyl ether (3:1)

Sources & evidence

ORD record
ord-24a293a4438a4d57a439e22e1a66c6ef
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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