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| | 3-Amino-1-adamantanol Basic information |
| | 3-Amino-1-adamantanol Chemical Properties |
| Melting point | 265 °C (dec.)(lit.) | | Boiling point | 266.8±23.0 °C(Predicted) | | density | 1.252±0.06 g/cm3(Predicted) | | Fp | 230 °F | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Crystalline Powder | | pka | 15.07±0.40(Predicted) | | color | White to yellow | | Water Solubility | Soluble in organic solvents,insoluble in water. | | InChI | InChI=1S/C10H17NO/c11-9-2-7-1-8(3-9)5-10(12,4-7)6-9/h7-8,12H,1-6,11H2 | | InChIKey | DWPIPTNBOVJYAD-UHFFFAOYSA-N | | SMILES | C12(O)CC3CC(CC(N)(C3)C1)C2 | | CAS DataBase Reference | 702-82-9(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29221990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 3-Amino-1-adamantanol Usage And Synthesis |
| Description | 3-Amino-1-adamantanol is an important adamantane drug intermediate mainly used in the synthesis of inhibitors with antihyperglycaemic properties for the preparation of Vildagliptin, a dipeptidyl peptidase 4 (DPP-4) inhibitor used in the treatment of type 2 diabetes. | | Chemical Properties | White solid | | Uses | It is employed in the synthesis of inhibitors with antihyperglycemic properties. vil- dagliptin is synthesised from 3-Amino-1-adamantanol. | | Uses | As reagent, 3-Amino-1-hydroxyadamantane can be used in the preparation of Vildagliptin. | | Uses | 3-Amino-1-hydroxyadamantane can be employed in the synthesis of inhibitors with antihyperglycemic properties. | | Synthesis | A preparation method of 3-amino-1-adamantanol comprises the following steps: (1) adding amantadine or a salt thereof to sulfuric acid at 10-30°C and adding a mixed acid dropwise to perform a nitration reaction to obtain a reaction liquid; (2) adding the reaction liquid to water and mixing the reaction liquid with water to obtain a mixed solution; (3) performing a hydroxylation reaction under the effect of alkaline to obtain the 3-amino-1-adamantanol. The preparation method employs the raw material, is easy to obtain, is simple in operations, is environmentally protective, is low in cost, and is high in yield, which is generally higher than 80%, maximally 90.1%. | | References | [1] Pharmaceutical Chemistry Journal, 1990, vol. 24, # 1, p. 35 - 39
[2] Khimiko-Farmatsevticheskii Zhurnal, 1990, vol. 24, # 1, p. 29 - 31
[3] Tetrahedron Letters, 2017, vol. 58, # 15, p. 1456 - 1458
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 947 - 964
[5] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 554 - 564 |
| | 3-Amino-1-adamantanol Preparation Products And Raw materials |
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