4-Toluenesulfonyl chloride → 1-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

HRID 2272530Notes

Reaction equation

HRID 2272530 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidineYield 86.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Methylbenzenesulfonyl chloride (52.1 g) was added to a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (50.0 g) in pyridine (248 mL) at room temperature. The mixture was stirred at room temperature overnight. After evaporation of the solvent, water and ethyl acetate were added to the residue. The organic layer was separated, washed with 1M hydrochloric acid and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was triturated in diisopropyl ether at 0 C (“C” represents “degrees Celsius”) to give the title compound (76.1 g).

Workup

  1. customAfter evaporation of the solvent, water and ethyl acetate
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. washwashed with 1M hydrochloric acid and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in diisopropyl ether at 0 C (“C” represents “degrees Celsius”)

Sources & evidence

ORD record
ord-5d7260c3784c4a94a3afa25bbd9e8796
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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