1-Methylcyclohexa-1,3-diene → 3,3-Difluoroazetidine-1-sulfonamide

HRID 1525673Notes

Reaction equation

HRID 1525673 reaction equation
[F:1][C:2]1([F:20])[CH2:5][N:4]([S:6]([NH:9]C(=O)OCC2C=CC=CC=2)(=[O:8])=[O:7])[CH2:3]1.CC1CCC=CC=1>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1([F:20])[CH2:5][N:4]([S:6]([NH2:9])(=[O:8])=[O:7])[CH2:3]1

Participants

5

Reactant 2

HCID 1217311-Methylcyclohexa-1,3-dieneHCID 89633252Benzyl (3,3-difluoroazetidin-1-yl)sulfonylcarbamate

Product 1

HCID 672167873,3-Difluoroazetidine-1-sulfonamideYield 91.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl (3,3-difluoroazetidin-1-yl)sulfonylcarbamate (Preparation 22, 800 mg, 2.61 mmol) in methanol (20 mL) was added 10% palladium hydroxide on charcoal (150 mg) and methylcyclohexadiene (4.9 g, 52.3 mmol) and the mixture heated at reflux for 18 hours. Once cooled the reaction mixture was filtered through Celite™ and concentrated to give the title compound as an amber oil (410 mg, 91%).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hours
  3. temperatureOnce cooled the reaction mixture
  4. filtrationwas filtered through Celite™
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-16a9c9c2348f4e20bb203de0fb0c32e9
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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