P-Toluenesulfonylhydrazide → HCID 117833149, compound

HRID 516654Notes

Reaction equation

HRID 516654 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([S:7]([NH:10][NH2:11])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:13]([O:17][C:18]([N:20]1[C:25]2([CH3:29])[CH2:26][CH2:27][CH2:28][C:21]1([CH3:31])[CH2:22][C:23](=O)[CH2:24]2)=[O:19])([CH3:16])([CH3:15])[CH3:14].O.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[C:13]([O:17][C:18]([N:20]1[C:21]2([CH3:31])[CH2:28][CH2:27][CH2:26][C:25]1([CH3:29])[CH2:24][C:23](=[N:11][NH:10][S:7]([C:4]1[CH:3]=[CH:2][C:1]([CH3:12])=[CH:6][CH:5]=1)(=[O:8])=[O:9])[CH2:22]2)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 15303P-ToluenesulfonylhydrazideHCID 86585896Sodium bicarbonate waterHCID 117833033HCID 117833033, compound

Product 1

HCID 117833149HCID 117833149, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Toluenesulfonyl hydrazine (6.37 g, 34.2 mmol) was added to a benzene solution (115 ml) of N-tert-butoxycarbonyl-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-one (3.04 g, 11.4 mmol), and the mixture was heated under reflux for 6 h with a Dean-Stark device. After adding saturated sodium bicarbonate water under ice-cooled condition, the ice-cooled reaction liquid was extracted with ethyl acetate, washed with saturated brine, and dried over magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography to give N-tert-butoxycarbonyl-1,5-dimethyl-3-(tosylhydrazono)-9-azabicyclo[3.3.1]nonane (3.07 g, 62%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 h with a Dean-Stark device
  3. temperaturecooled condition
  4. customreaction liquid
  5. extractionwas extracted with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationAfter concentration under reduced pressure
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-06f65933c760490ba121feca809619fb
Source dataset
uspto-grants-2015_08
Patent number
US09114390B2

Reaction notes

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