Idramantone → 5-Hydroxy-adamantan-2-one oxime

HRID 1990989Notes

Reaction equation

HRID 1990989 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=O)[CH2:3]1)[CH2:9]2.Cl.[NH2:14][OH:15]>CCO.[OH-].[Na+]>[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[N:14][OH:15])[CH2:3]1)[CH2:9]2

Participants

5

Reactant 2

HCID 64184IdramantoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 230089835-Hydroxy-adamantan-2-one oximeYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

5-Hydroxyadmantan-2-one (TCI America, Portland, Oreg.; 3 g, 18.0 mmol) was dissolved in EtOH (20 mL) and the solution was added to a solution of hydroxylamine hydrochloride (12 g, 172.7 mmol) in 1N NaOH (16 mL). The mixture was heated at 100° C. for 1 hour. The EtOH was evaporated, and water and DCM were added. The separated aqueous layer was further extracted twice with DCM. The combined DCM layers were evaporated under vacuum. Crystallization from EtOAc gave 5-hydroxy-adamantan-2-one oxime (2.3 g, 71%).

Workup

  1. customThe EtOH was evaporated
  2. additionwater and DCM were added
  3. extractionThe separated aqueous layer was further extracted twice with DCM
  4. customThe combined DCM layers were evaporated under vacuum
  5. customCrystallization from EtOAc

Sources & evidence

ORD record
ord-fd671fa92bdc40ee886bca327b613883
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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