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

HRID 1374851Notes

Reaction equation

HRID 1374851 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[CH3:26][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 106428511-(tert-Butoxycarbonyl)-4-((p-toluenesulfonyloxy)methyl)piperidineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl 4-hydroxymethylpiperidine-1-carboxylate (prepared by referring to Japanese Patent Unexamined Publication No. 11-217377, 12.12 g, 56.30 mmol) was dissolved in dichloromethane (26 ml), and the solution was added with p-toluenesulfonyl chloride (10.73 g, 56.30 mmol) and triethylamine (8.63 mmol, 61.9 mmol) at room temperature, and then stirred at the same temperature for 5 hours. The reaction mixture was diluted with dichloromethane (100 ml) and washed with water and saturated brine, and dried over sodium sulfate. Insoluble solids were removed by filtration and the filtrate was evaporated under reduced pressure. The residue was recrystallized from hexane (100 ml) to obtain the title compound as colorless solid (14.13 g, yield: 85%).

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over sodium sulfate
  3. customInsoluble solids were removed by filtration
  4. customthe filtrate was evaporated under reduced pressure
  5. customThe residue was recrystallized from hexane (100 ml)

Sources & evidence

ORD record
ord-847ef787076e4507b1e907aae2bfd8ec
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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