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

HRID 856074

Reaction equation

HRID 856074 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.CN(C)CCCCCCN(C)C.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(#N)C.O>[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)(=[O:42])=[O:41])=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8097TetramethylhexamethylenediamineHCID 8471TriethylamineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidineYield 117%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Tert-butyl 4-hydroxypiperidine-1-carboxylate (2.22 g, 10.0 mmol) was dissolved in acetonitrile (40 ml), to which triethylamine (2.74 ml, 19.7 mmol) and N,N,N′,N′-tetramethyl-1,6-diaminohexane (0.57 ml, 2.64 mmol) were added, and the mixture was cooled in an ice-bath. p-Toluenesulfonyl chloride (2.75 g, 14.4 mmol) was added to this mixture, which was allowed to return to room temperature and stirred overnight. Water was poured into the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) to afford tert-butyl 4-(toluene-4-sulfonyloxy)piperidine-1-carboxylate (4.16 g, yield 89%) as a pale yellow powder.

Workup

  1. additionwere added
  2. temperaturethe mixture was cooled in an ice-bath
  3. customto return to room temperature
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)

Sources & evidence

ORD record
ord-beb8af66e5a848a6bc3a2c86a25f5c8a
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Linked notes

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