3-Hydroxy-1-AdaMantane Carboxylic Acid Chemical Properties

Melting point:

203 °C

Boiling point:

357.2±25.0 °C(Predicted)

Density 

1.419±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.60±0.40(Predicted)

color 

Off-White

InChI

InChI=1S/C11H16O3/c12-9(13)10-2-7-1-8(3-10)5-11(14,4-7)6-10/h7-8,14H,1-6H2,(H,12,13)

InChIKey

CJJMAWPEZKYJAP-UHFFFAOYSA-N

SMILES

C12(C(O)=O)CC3CC(CC(O)(C3)C1)C2

CAS DataBase Reference

42711-75-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-37/39-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29181990

MSDS

• Language:English Provider:ALFA

3-Hydroxy-1-AdaMantane Carboxylic Acid Usage And Synthesis

Chemical Properties

White to yellow solid

Uses

1-Carboxy-3-adamantanol is used in the synthesis of potent pyridyl amide/sulfonamide inhibitors of 11β-HSD-1 which could be applied to a treatment of ulcers or in hormone therapy treatments relating to cortisol.

Uses

3-Hydroxy-1-AdaMantane Carboxylic Acid is used in the synthesis of potent pyridyl amide/sulfonamide inhibitors of 11β-HSD-1 which could be applied to a treatment of ulcers or in hormone therapy treatments relating t o cortisol.

Synthesis Reference(s)

Synthetic Communications, 18, p. 1967, 1988 DOI: 10.1080/00397918808068263

Synthesis

The general procedure for the synthesis of 3-hydroxyadamantane from 1-adamantanecarboxylic acid was as follows: 30.2 g of 1-adamantanol (99% purity) was added to a glass reaction flask equipped with a stirrer, a thermometer, a dropping funnel, and a Dimroth condenser, followed by the addition of 215.2 g of 96% concentrated sulfuric acid. After stirring at room temperature until the ingredients were completely dissolved, 9.3 g of formic acid was slowly added dropwise over a period of 15 minutes and the temperature of the reaction solution was maintained between 10 and 20 °C by external cooling. After the dropwise addition, the reaction temperature was raised to 35 °C for 3 hours. The progress of the reaction was monitored by gas chromatography (GC) and 1-adamantanecarboxylic acid was produced when the conversion of 1-adamantanol reached 100%. Subsequently, 23.1 g of 70% nitric acid was slowly added dropwise over a period of 30 min under continued cooling conditions, maintaining the temperature of the reaction solution in the range of 10 to 20 °C. After completion of the dropwise addition, the reaction temperature was maintained at 35 °C for 3 hours to continue the reaction. After confirming the complete conversion of 1-adamantanecarboxylic acid to 3-hydroxyadamantane-1-carboxylic acid by GC, the subsequent purification step was carried out. Purification step: in another glass flask equipped with a stirrer and a thermometer, a mixed solution of sodium hydroxide and sodium sulfite was prepared by adding 90.2 g of sodium hydroxide, 35.5 g of sodium sulfite and 812 g of ion-exchanged water, and the flask was cooled. 277.8 g of reaction solution containing 3-hydroxy-1-adamantanecarboxylic acid was slowly added to the above mixed solution, and the temperature of the liquid was controlled not to exceed 40 ℃. The precipitated white crystals were separated by filtration and washed with deionized water. The resulting crystals were dried under reduced pressure at 40 °C for 8 h. Finally, 35.8 g (92.6% yield) of white crystals of 3-hydroxyadamantane-1-carboxylic acid were obtained. The content of high boiling point by-products (high molecular weight by-products) in the crystals was 1.28% as analyzed by gel permeation chromatography-refractive index detector (GPC-RI).

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 1, p. 98 - 118
[2] Patent: JP2016/84315, 2016, A. Location in patent: Paragraph 0043-0045
[3] Letters in Organic Chemistry, 2016, vol. 13, # 7, p. 514 - 518
[4] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 10, p. 1680 - 1683
[5] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 10, p. 2098 - 2102

3-Hydroxy-1-AdaMantane Carboxylic Acid(42711-75-1)Related Product Information

• 1-Adamantanol
• 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3S,5R)-
• (S) - N- Boc- adamantylglycine
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• axagliptin Impurity 28 Mesylate
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• Saxagliptin Impurity 4 (Deoxy Saxagliptin)
• Saxagliptin Impurity 24
• Saxagliptin IMpurity 1
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• (1S,3S,5S)-2-(TERT-BUTOXYCARBONYL)-2-AZABICYCLO[3.1.0]HEXANE-3-CARBOXYLIC ACID
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• 1H-Pyrrole-1-carboxylic acid, 2-(aMinocarbonyl)-2,3-dihydro-, 1,1-diMethylethyl ester, (2S)-