1-Tert-butoxycarbonyl-4-(3-methanesulfonyloxypropoxy)piperidine → 4-(3-methoxypropyloxy)-N-t-butyloxycarbonylpiperidine

HRID 1816715Notes

Reaction equation

HRID 1816715 reaction equation
CS([O:5][CH2:6][CH2:7][CH2:8][O:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)(=O)=O.[CH3:23]O.C[O-].[Na+]>CO>[CH3:23][O:5][CH2:6][CH2:7][CH2:8][O:9][CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 224946651-Tert-butoxycarbonyl-4-(3-methanesulfonyloxypropoxy)piperidineHCID 23694274Sodium methanolate methanol

Product 1

HCID 224946674-(3-methoxypropyloxy)-N-t-butyloxycarbonylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[3-(methanesulfonyloxy)propyloxy]-N-t-butyloxycarbonylpiperidine (3.76 g) in methanol (20 ml) was added 28% sodium methoxide methanol solution (22.7 ml), and the mixture was stirred under refluxing for 1.5 hours. The reaction mixture was evaporated in vacuo and dissolved in ethyl acetate (200 ml). The solution was washed twice with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (200 ml) eluting with a mixture of n-hexane and ethyl acetate (2:1 v/v). The fractions containing the object compound were collected and evaporated under reduced pressure to give 4-(3-methoxypropyloxy)-N-t-butyloxycarbonylpiperidine (2.66 g).

Workup

  1. temperatureunder refluxing for 1.5 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutiondissolved in ethyl acetate (200 ml)
  4. washThe solution was washed twice with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe resulting residue was chromatographed on silica gel (200 ml)
  8. washeluting with a mixture of n-hexane and ethyl acetate (2:1 v/v)
  9. additionThe fractions containing the object compound
  10. customwere collected
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1ddfa5733be44a64b3fcbd4f7d1b98ae
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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