1-Methylimidazole → 1-(4-Chlorobenzyl)-3-(4-toluenesulfonyloxy)methyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl ester

HRID 922735Notes

Reaction equation

HRID 922735 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9][CH2:8][C:7]([CH2:11][OH:12])([CH3:10])[C:6]1=[O:13])=[O:4].C(N(CC)CC)C.CN1C=CN=C1.[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]([C:5]1([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:9][CH2:8][C:7]([CH2:11][O:12][S:41]([C:38]2[CH:39]=[CH:40][C:35]([CH3:45])=[CH:36][CH:37]=2)(=[O:43])=[O:42])([CH3:10])[C:6]1=[O:13])=[O:4]

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 672540121-(4-Chlorobenzyl)-3-hydroxymethyl-3-methyl-2-oxocyclopentanecarboxylic acid methyl ester

Product 1

HCID 867182551-(4-Chlorobenzyl)-3-(4-toluenesulfonyloxy)methyl-3-methyl-2-oxo-cyclopentancarboxylic acid methyl esterYield 75.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In 95 ml of toluene, 4.756 g of Compound 2-1 obtained in Production Example 1 was dissolved. To the solution thus obtained, 3.12 ml of triethylamine and 1.76 ml of N-methylimidazole were added, and 3.38 g of 4-toluenesulfonyl chloride was added. The resulting mixture was stirred at room temperature for 100 minutes. After the reaction, water was added to the reaction solution thus obtained, and the organic layer was separated from the suspension. Thereafter, the aqueous layer was extracted with toluene and then blended with the organic layer previously obtained. The resultant organic layer thus obtained was washed with an aqueous solution of 1 mol/l hydrochloric acid and saturated brine and then dried over anhydrous sodium sulfate. The solvent was distilled away, and the residue was then purified by silica gel column chromatography to obtain 5.397 g of Compound 3-1-2.

Workup

  1. dissolutionwas dissolved
  2. customTo the solution thus obtained
  3. additionwas added to the reaction solution
  4. customthus obtained
  5. customthe organic layer was separated from the suspension
  6. extractionThereafter, the aqueous layer was extracted with toluene
  7. custompreviously obtained
  8. customThe resultant organic layer thus obtained
  9. washwas washed with an aqueous solution of 1 mol/l hydrochloric acid and saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThe solvent was distilled away
  12. customthe residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b36ebe72e0254bafb75aae5438d2d478
Source dataset
uspto-grants-2016_03
Patent number
US09278966B2

Reaction notes

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