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

HRID 649403Notes

Reaction equation

HRID 649403 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-toluenesulfonate

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 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 2N-hydrochloric acid and 500 ml of 1N hydrochloric acid successively, further with dilute aqueous sodium hydrogencarbonate 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 2N-hydrochloric acid and 500 ml of 1N hydrochloric acid successively
  5. dry with materialfurther with dilute aqueous sodium hydrogencarbonate 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-21bf55dc825c438f9e23fff32370ad94
Source dataset
uspto-grants-1988_04
Patent number
US04739066

Reaction notes

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