Hydrogen Peroxide → 2-Chloro-5-(oxiranylmethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1765532Notes

Reaction equation

HRID 1765532 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]=[CH2:24])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].N1C=CC=N1.[OH:30]O.O>ClCCl.C[Re](=O)(=O)=O>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]2[CH2:24][O:30]2)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Participants

7

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 1048Pyrazole2×HCID 211074042-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 211074132-Chloro-5-(oxiranylmethyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 5a) (9.4 g), pyrazole (0.45 g) and methyltrioxorhenium(VII) (0.40 g) were stirred together in dichloromethane (40 mL) under nitrogen, and hydrogen peroxide (27.5% wt. solution in water, 13 mL) was added dropwise. The reaction was then monitored by HPLC/MS and further portions of pyrazole, methyltrioxorhenium(VII) and hydrogen peroxide were added over a period of 2 days until the reaction mixture consisted of a 1:1 mixture of starting material and product. The mixture was then poured into water (500 mL), extracted into dichloromethane (3×300 mL), washed with 2M aqueous hydrochloric acid (300 mL), brine (300 mL), saturated aqueous sodium thiosulfate (300 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to give an oil. This was purified by column chromatography eluting with 2:1 isohexane/ethyl acetate to give the sub-titled compound (4.71 g).

Workup

  1. additionwere added over a period of 2 days until the reaction mixture
  2. additionconsisted of a 1:1 mixture of starting material and product
  3. extractionextracted into dichloromethane (3×300 mL)
  4. washwashed with 2M aqueous hydrochloric acid (300 mL), brine (300 mL), saturated aqueous sodium thiosulfate (300 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil
  9. customThis was purified by column chromatography
  10. washeluting with 2:1 isohexane/ethyl acetate

Sources & evidence

ORD record
ord-76bf1b84614a4a3387630426baed0903
Source dataset
uspto-grants-2007_06
Patent number
US07227038B2

Reaction notes

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