Description

5-Hydroxy-2-adamantanone (5-hydroxyadamantan-2-one) is a versatile starting material for synthesising various 2,5- or 1,4-disubstituted adamantanes. Chemical methods for synthesizing 5-hydroxy-2-adamantanone include disproportionation of 2-hydroxyadamantane and oxidation of 2-adamantanone. A synthetic approach to produce 5-hydroxy-2-adamantanone using P450cam (CYP101A1; a camphor monooxygenase) coupled with NADH regeneration as an oxidation biocatalyst has been reported[1].

Chemical Properties

White crystal or crystalline powder

Uses

5-Hydroxy-2-adamantanone may be used in the following studies:

• As a model compound to investigate the application of lanthanide NMR shift reagents for the analysis of disubstituted derivative of adamantane.
• As a starting material for the synthesis of E-2-amino-5-hydroxyadamantane.
• As a starting material for the synthesis of 4-(triphenylsilyloxy)adamantan-1-ol.

Uses

anthelmintic

Definition

ChEBI: Idramantone is a member of adamantanones.

brand name

INDICLOR (Nycomed Amersham).

General Description

5-Hydroxy-2-adamantanone is a disubstituted derivative of adamantane. The biocatalyzed synthesis of 5-hydroxy-2-adamantanone from 2-adamantanone has been investigated.

Synthesis

700-58-3

20098-14-0

Step (i): Synthesis of 5-hydroxy-2-adamantanone (compound of formula 11) Under cooling in an ice bath, adamantanone (50 g, 333 mmol) was slowly added to concentrated nitric acid (98%, 440 mL) for 15 min while stirring was maintained. The reaction mixture was stirred continuously for 72 h at room temperature and then warmed to 60 °C for 2 h until most of the nitrogen dioxide gas escaped. Excess nitric acid was removed by distillation under reduced pressure and the resulting pale yellow oil solidified on cooling. The reaction mixture was sequentially diluted with deionized water (200 mL) and concentrated sulfuric acid (75 mL), and the resulting clarified yellow solution was heated on a steam bath in a fume hood for 1 hour. The reaction solution was neutralized with 30% aqueous sodium hydroxide under warm conditions and subsequently extracted with chloroform. The organic phases were combined, washed with saturated saline and concentrated under reduced pressure. The crude product was dissolved in dichloromethane (15 mL), hexane was added dropwise until the precipitate was no longer generated, the solid was collected by filtration and dried under vacuum to give 5-hydroxy-2-adamantanone (compound of formula 11, 40.9 g) in 74% yield. Characterization data: Melting point: 278.8-300°C; 1H-NMR (CDCl3) δ: 2.69 (bs, 2H), 2.36-2.32 (m, 2H), 2.12-2.02 (m, 2H), 2.02-1.88 (m, 6H), 1.80-1.68 (m, 1H); IR (cm-1): 3410, 2929, 2855, 2645, 1725, 1539, 1452, 1351, 1288, 1116, 1055, 927, 900, 797; Mass spectrum (m/z): 167 [M+H]+.

References

[1] Toshiki Furuya . “Biocatalytic production of 5-hydroxy-2-adamantanone by P450cam coupled with NADH regeneration.” Journal of Molecular Catalysis B-enzymatic 94 (2013): Pages 111-118.