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

HRID 1928536Notes

Reaction equation

HRID 1928536 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-ca5c116d8d964259a7ff23246477fc7b
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Reaction notes

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