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

HRID 280983Notes

Reaction equation

HRID 280983 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

To a chilled mixture of 5-(1-benzyloxycarbonyl-4-piperidyl)pentanol (18 g) and pyridine (150 ml) is added portionwise tosyl chloride (14.6 g) for 30 minutes with stirring. After stirring for further 1 hour at ice-bath temperature, ice water (2 ml) is added dropwise and the resulting mixture is dissolved in ethyl acetate (500 ml). This solution is washed successively with 2N hydrochloric acid (500 ml), 1N hydrochloric acid (500 ml×2), sodium bicarbonate solution and water. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue is purified by silica gel column chromatography using hexane-ethyl acetate (3:1-2:1) to give 5-(1-benzyloxycarbonyl-4-piperidyl)pentyl p-toluenesulfonate (18 g) as an oil.

Workup

  1. additionis added dropwise
  2. washThis solution is washed successively with 2N hydrochloric acid (500 ml), 1N hydrochloric acid (500 ml×2), sodium bicarbonate solution and water
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oily residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e1144214601b4f36a6dc9565a81ea8f0
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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