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

HRID 1751799Notes

Reaction equation

HRID 1751799 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:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([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:23])=[O:22])=[CH:17][CH:16]=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 85.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5 g tert-butyl 4-hydroxypiperidine-1-carboxylate are placed in 15 ml of pyridine, then 4.7 g p-toluenesulphonyl chloride are added batchwise. The reaction mixture is stirred at ambient temperature, after 12 hours it is poured onto ice water and the mixture obtained is stirred for a further hour at ambient temperature. The precipitated solid is suction filtered and dried. 7.5 g product are obtained.

Workup

  1. additionis poured onto ice water
  2. customthe mixture obtained
  3. stirringis stirred for a further hour at ambient temperature
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-d2e0ce47cc3c4ee0bbd936f43df68a9e
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

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