Pyridine → 5-(1-Benzyloxycarbonyl-4-piperidyl)pentylp-toluenesulfonate

HRID 980613Notes

Reaction equation

HRID 980613 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[S:29](Cl)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30]>C(OCC)(=O)C>[C:35]1([CH3:36])[CH:37]=[CH:38][C:32]([S:29]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:14]2[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[CH2:12][CH2:13]2)(=[O:31])=[O:30])=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 140469305-(1-Benzyloxycarbonyl-4-piperidyl)pentanol

Product 1

HCID 201436535-(1-Benzyloxycarbonyl-4-piperidyl)pentylp-toluenesulfonateYield 66.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 18 g of 5-(1-benzyloxycarbonyl-4-piperidy)pentanol and 150 ml of pyridine is stirred under ice-cooling, and 14.6 g of tosyl chloride is added portionwise to the mixture over the period of 30 minutes. After stirring for another 1 hour under ice-cooling, 2 ml of ice-cold water is added dropwise. Ethyl acetate (500 ml) is added to the reaction solution, which is then washed with 500 ml of 2 N-hydrochloric acid and 500 ml of 1 N hydrochloric acid successively, further with dilute aqueous sodium hydrogen-carbonate solution and water successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily material is purified by silica-gel column chromatography to give 18 g of 5-(1-benzyloxycarbonyl-4-piperidyl)pentyl p-toluenesulfonate as an oily material.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for another 1 hour under ice-
  3. temperaturecooling
  4. washis then washed with 500 ml of 2 N-hydrochloric acid and 500 ml of 1 N hydrochloric acid successively
  5. dry with materialfurther with dilute aqueous sodium hydrogen-carbonate solution and water successively, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oily material is purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-1cb77232808249c9b566afb7e495d902
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

Loading…