Triethylamine → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

HRID 216714Notes

Reaction equation

HRID 216714 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (25.55 g, 123 mmol) in CH2Cl2 (250 ml), cooled to 0° C., is slowly added Et3N (18.95 ml, 135.4 mmol) followed by methane sulfonyl chloride (9.569 ml, 123.14 mmol) and DMAP (152 mg, 1.23 mmol). The mixture is stirred at room temperature overnight. The suspension is diluted with CH2Cl2 and the phases are separated. The aqueous phase is re-extracted 3× with CH2Cl2. The combined organic layers are washed with brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. Upon concentration, the desired compound precipitates and is collected by filtration to afford, after drying in HV, the title compound as a colorless solid.

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is re-extracted 3× with CH2Cl2
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. concentrationUpon concentration
  8. customthe desired compound precipitates
  9. filtrationis collected by filtration
  10. customto afford
  11. customafter drying in HV

Sources & evidence

ORD record
ord-1aabfc7dfd444a298275d57da7e84aaf
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

Loading…