4-Toluenesulfonyl chloride → HCID 20163367, compound

HRID 256289Notes

Reaction equation

HRID 256289 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH3:7])[CH2:3]1.C(N(CC)CC)C.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>C(Cl)Cl>[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([O:1][CH:2]2[CH2:6][CH2:5][N:4]([CH3:7])[CH2:3]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 930741-Methyl-3-pyrrolidinol

Product 1

HCID 20163367HCID 20163367, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3.0 g (0.03 mole) of 3-hydroxy-1-methylpyrrolidine, 3.1 g (0.03 mole) of triethylamine, and 25 mL of methylene chloride was added 5.6 g (0.03 mole) of 4-methylphenylsulfonyl chloride, and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated to a residue. The residue was dissolved in ether, the solution filtered, and the filtrate concentrated to give 5.75 g of product as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated to a residue
  2. dissolutionThe residue was dissolved in ether
  3. filtrationthe solution filtered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d8deb56c1a0c49e3a13c3db8cfe16add
Source dataset
uspto-grants-1987_10
Patent number
US04702763

Reaction notes

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