Hydroxyamine hydrochloride → N-[(1S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ylidene]hydroxylamine

HRID 582917Notes

Reaction equation

HRID 582917 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[CH3:9][C@@:10]12[C:16](=O)[C:15]([CH3:19])([CH3:18])[C@@H:13]([CH2:14]1)[CH2:12][CH2:11]2>O.CO>[CH3:9][C@@:10]12[CH2:14][CH:13]([CH2:12][CH2:11]1)[C:15]([CH3:19])([CH3:18])[C:16]2=[N:2][OH:3]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 1201521d-Fenchone

Product 1

HCID 71362104N-[(1S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ylidene]hydroxylamineYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 23 g of hydroxylamine hydrochloride and 41 g of sodium acetate in 200 ml of water is added at RT to a solution of 38.1 g of (1S)-(+)-fenchone in 120 ml of MeOH and the mixture is then refluxed for 48 hours. After cooling to RT, the precipitate formed is filtered off, washed with water and dried under vacuum to give 41 g of the expected product.

Workup

  1. temperaturethe mixture is then refluxed for 48 hours
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-d68ee45e103d4ea48d0b855e928f69fb
Source dataset
uspto-grants-1999_07
Patent number
US05925768

Reaction notes

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