Sulfuric Acid → 1-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

HRID 1914244Notes

Reaction equation

HRID 1914244 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.OS(O)(=O)=O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:32][C:22]1[CH:27]=[CH:26][C:25]([S:28]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)(=[O:30])=[O:29])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

201 g tert-Butyl 4-hydroxypiperidine-1-carboxylate, 160 ml triethylamine and 6.0 g 4-dimethylaminopyridine are dissolved in 750 ml DCM. 191 g 4-toluenesulfonylchloride is added and the mixture is refluxed for 7 h. The mixture is cooled in ice and acidified with 100 ml of 1M H2SO4; the organic layer is washed with 300 ml of water (twice), 250 ml of 1 M Na2CO3 solution (twice), dried over MgSO4, filtered and concentrated in vacuo.

Workup

  1. temperaturethe mixture is refluxed for 7 h
  2. temperatureThe mixture is cooled in ice
  3. washthe organic layer is washed with 300 ml of water (twice), 250 ml of 1 M Na2CO3 solution (twice),
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-486fbfa69e4e44a381d36927c13add6b
Source dataset
uspto-grants-2013_12
Patent number
US08609848B2

Reaction notes

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