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

HRID 1894360Notes

Reaction equation

HRID 1894360 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>N1C=CC=CC=1>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidineYield 102.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-Boc-4-piperidinemethanol (5.69 g, 26.43 mmol, Aldrich) in pyridine (50 mL) cooled to 0° C. was added tosyl chloride (10.077 g, 52.86 mmol). The reaction mixture was stirred for 3 h. The mixture was then poured into ice water and stirred vigorously. The product was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated to give a light pink oil as crude product of 4-(toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (10 g). It was used without further purification.

Workup

  1. stirringstirred vigorously
  2. extractionThe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solids were filtered off
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-84b43cdd0aaa41898a672929244c7545
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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