4-Toluenesulfonyl chloride → N-Boc-4-[2-(4-Toluenesulfonyloxy)ethyl]piperidine

HRID 655592Notes

Reaction equation

HRID 655592 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=2)(=[O:32])=[O:31])[CH2:10][CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 21936070N-Boc-4-[2-(4-Toluenesulfonyloxy)ethyl]piperidineYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of N-Boc-4-piperidine-ethanol (5.0 g, 21.8 mmol) and Et3N (4.6 mL, 33.0 mmol) in dry DCM (10 mL) was added p-toluenesulfonyl chloride (6.25 g, 32.8 mmol) slowly. Upon addition, the reaction was warmed to room temperature and stirred for 20 h. The reaction mixture was washed with water (40 mL), 10% (wt/v) citric acid(aq) (40 mL), and saturated NaHCO3(aq) (40 mL). The DCM layer was dried with MgSO4, filtered and concentrated in vacuo to give a pale yellow oil, which was chromatographed to give the title compound (7.47 g, 89% yield) as a clear and colorless oil.

Workup

  1. additionUpon addition
  2. washThe reaction mixture was washed with water (40 mL), 10% (wt/v) citric acid(aq) (40 mL), and saturated NaHCO3(aq) (40 mL)
  3. dry with materialThe DCM layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a pale yellow oil, which
  7. customwas chromatographed

Sources & evidence

ORD record
ord-bcde2c1edd604a37a9bd7c91469ee2b8
Source dataset
uspto-grants-2011_12
Patent number
US08071602B2

Reaction notes

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