Water → 1-Tert-butoxycarbonyl-4-(3-methanesulfonyloxypropoxy)piperidine

HRID 1816714Notes

Reaction equation

HRID 1816714 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][O:5][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.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>C(OCC)(=O)C>[CH3:26][S:27]([O:1][CH2:2][CH2:3][CH2:4][O:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22494654Tert-butyl 4-(3-hydroxypropoxy)piperidine-1-carboxylate

Product 1

HCID 224946651-Tert-butoxycarbonyl-4-(3-methanesulfonyloxypropoxy)piperidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-(3-hydroxypropyloxy)-N-t-butyloxycarbonylpiperidine (3.82 g) in ethyl acetate (40 ml) were added triethylamine (4.1 ml) and methanesulfonyl chloride (1.37 ml) with stirring under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture were added water (50 ml) and ethyl acetate (50 ml) with stirring. The organic layer was separated, washed twice with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (150 ml) eluting with a mixture of n-hexane and ethyl acetate (1:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give 4-[3-(methanesulfonyloxy)propyloxy]-N-t-butyloxycarbonylpiperidine (3.77 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. stirringwith stirring
  4. customThe organic layer was separated
  5. washwashed twice with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customThe resulting residue was chromatographed on silica gel (150 ml)
  9. washeluting with a mixture of n-hexane and ethyl acetate (1:1 v/v)
  10. additionThe fractions containing the desired compound
  11. customwere collected
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3b48b2a65032447cadd512d0a153754c
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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