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CAS No. : | 62058-03-1 | MDL No. : | MFCD12761603 |
Formula : | C10H17NO | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 167.25 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In water; at 20℃; | A mixture of 2,5-dihydro-2,5-dimethoxy- furan (0.01 mol) and 4-amino-, (la,3a,4a,5i,7a)- tricyclo[3.3.1. 13,7]decan-l-ol (0.01 mol) in water (50 ml) was stirred at room temperature. Hydrochloric acid concentrated (2 ml) was added and the reaction mixture was stirred overnight. The acidic mixture was neutralized with an aqueous NaHC03 solution. This mixture was extracted with DCM (3 x). The combined organic layers were dried, filtered and the solvent evaporated, yielding 1.5 g of intermediate 13. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2h; | Example IB E-2-bromo-N-r5-hvdroxy-adamantan-2-ylV2-methyl-propionamide; A solution of E- and Z-5-hydroxy-2-adamantamine (0.868g, 5.2 mmoles) in DCM (15.0 mL) and DIPEpsilonA (2.5 mL) was cooled in an ice bath and treated with 2-bromoisobutyryl bromide (0.72 mL, 5.8 mmoles) in DCM (2.5 mL). The mixture was stirred for 2 hours at room temperature and DCM was removed under reduced pressure. The residue was partitioned between water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, water, dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to provide the title compound as dark beige solid (1.17 g, 71percent). The isomers were separated by column chromatography (silica gel, 5-35percent acetone in hexane) to furnish 0.78 g of E-2-bromo-N-(5-hydroxy-adamantan-2-yl)-2-methyl-propionamide and 0.39 g of Z-2-bromo-N-(5-hydroxy-adamantan-2-yl)-2-methyl-propionamide.Example 1C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 24h; | To a solution of Compound 21(181mg) in dimethyl formamide were added hydroxy adamantanamine(94mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(118mg), 1-hydroxybenzotriazole(21mg) and triethylamine(121mul), then the resulting solution was stirred at room temperature for 24hrs. After termination of the reaction, the solution was diluted with 2N HCl aqueous soln. and extracted with ethyl acetate. The organic layer was washed with sat. sodium hydrogencarbonate soln. and brine successively, and dried with magnesium sulfate. The residue was purified by silicagel columnchromatography to give Compound 22(176mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 13h; | To a solution of Compound 29(102mg) in methylene chloride(2ml) were added hydroxy adamantanamine(81mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(82mg), 1-hydroxybenzotriazole(14mg) and triethylamine(115mul), then the resulting solution was stirred at room temperature for 13hrs. After termination of the reaction, the solution was acidified with 2N HCl aqueous soln. and extracted with methylene chloride. The organic layer was washed with sat. sodium hydrogencarbonate soln. and brine successively, and dried with sodium sulfate. The residue was purified by silicagel columnchromatography to afford Compound C-202(123mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h; | To a solution of Compound 32(193mg) in dimethyl formamide(4ml) were added hydroxy adamantanamine(152mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(155mg), 1-hydroxybenzotriazole(26mg) and triethylamine(217mul), then the resulting solution was stirred at room temperature for 18hrs. After termination of the reaction, the solution was acidified with 2N HCl aqueous soln. and extracted with methylene chloride. The organic layer was washed with sat. sodium hydrogencarbonate soln. and brine successively, and dried with sodium sulfate. The residue was purified by silicagel columnchromatography to give Compound C-186(36mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; | Example 37; [Show Image] According to the above scheme, Compound C-159 was synthesized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 14h; | Example 8; [Show Image] To a dimethylformamide solution (DMF) (5 ml) of a compound V-1 (150 mg) were added monohydroxy-2-adamantamine (140 mg), 1-hydroxybenzotriazole (HOBT) (31 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (WSC) (174 mg), and triethylamine (TEA) (180 mul) under the nitrogen atmosphere, and the mixture was stirred at room temperature for 14 hours. After completion of the reaction, 2N hydrochloric acid (30 ml) was added thereto followed by extraction with ethyl acetate. The organic layer was washed successively with aqueous saturated sodium hydrogen carbonate solution and saturated brine, and dried with magnesium sulfate. A solvent was evaporated, and the residue was purified by silica gel chromatography to obtain a compound VI-1 (226 mg). 1H NMR: (CDCl3); d 1.06 (d, J = 6.6 Hz, 6H), 1.53 - 2.20 (m, 14H), 3.72 (s, 3H), 3.98 (d, J = 6.6 Hz, 2H), 6.25 - 6.30 (m, 1H), 7.71 (s, 1H).(Reference Example 1) The mother washed liquid at filtration obtained in Example 2 was concentrated under reduced pressure, the solvent was evaporated, thereafter, silica gel chromatography (chloroform : methanol = 100 : 0 to 94 : 6) was performed, and fraction solutions corresponding to the formula (III-1'): |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen;palladium on activated charcoal; In tetrahydrofuran; for 2.5h; | Example 3; [Show Image] [Show Image] A compound III-1 (150 mg) was dissolved in tetrahydrofuran (3 ml), 10percent palladium carbon (30 mg) was added thereto, and hydrogen gas was introduced therein for 2.5 hours. After the catalyst was filtered, the filtrate was evaporated under reduced pressure to obtain the residue of a compound IV (100 mg, crude yield = 102.6percent). Compound (IV) 1H NMR (300 MHz, d6-DMSO): d 1.17 - 1.95 (m, 11H), 2.50 (m, 2H), 2.84 (brs, 1H). 13C NMR (75.4 MHz, CDCl3): d 29.3 (2C), 30.0 (1C), 36.8 (2C), 44.8 (2C), 45.6 (1C), 54.3 (1C), 67.5 (1C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example B.18 a) Preparation of compound 43; To a mixture of 2-(3-chlorophenoxy)-2-methyl-propanoic acid [17413-73-9] (0.010 mol) and CH2Cl2 (70 ml), HOBt (0.012 mol) was added at room temperature. The mixture was stirred until complete dissolution of HOBt. EDCI (0.012 mol) was added and the mixture was stirred at room temperature for 30 minutes. (lalpha,3alpha,4alpha,5beta,7alpha)- 4-aminotricyclo[3.3.1.13'7]decan-l-ol [62058-03-1] (0.012 mol) was added and the mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was dissolved in CH2CI2 and washed with 15percent citric acid solution, IM Na2CO3 and water. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography (eluent: CH2C12/CH3OH 100/0 to 98/2). Two product fraction groups were collected and the solvents were evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 1.97g of compound 43. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example B .5 Preparation of compound 6; iV-(ethylcarbonimidoyl)-iV,iV-dimethyl-l,3-propanediamine, monohydrochloride [25952-53-8] (0.0022 mol) and 1 -hydroxy- lH-benzotriazole (0.0022 mol) were added to a solution of intermediate 6 [212578-38-6] (0.002 mol) in DMF (25 ml) and the mixture was stirred and warmed (40°C). Then a solution of 4-amino- (lalpha,3alpha,4alpha,5beta,7alpha) tricyclo[3.3.1.13'7]decan-l-ol [62058-03-1] (0.0024 mol) in hot DMF was added and the reaction mixture was stirred overnight at room temperature. The mixture was poured out into ice-water and was extracted with EtOAc. The obtained extract was washed with water and with brine and then dried and concentrated, yielding 0.040 g of compound 6. Example B .6 |
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