Tricyclo[3.3.1.13,7]decane-1-carboxamide

White Solid

To a stirred mixture of 1-adamantanecarboxylic acid (11, 36.05 g, 200 mmol) and DMF (5 drops)in CH2Cl2 (360 mL) cooled in an ice-water bath was added thionyl chloride (26.17 g, 220 mmol) inone portion. The resulting mixture was refluxed until the evolution of HCl gas ceased (typicallywithin 2 h). The solvent and excess thionyl chloride were then removed on a rotary evaporator, andthe crude acid chloride 12 was dissolved in THF (100 mL). The resulting solution was then slowlyadded dropwise to stirred concentrated aqueous ammonia (400 mL) cooled in an ice-water bath.After addition, the resulting white slurry was stirred at room temperature for another 2 h, and thewhite precipitates were collected via vacuum filtration, washed with cold n-hexane and dried invacuo to afford 1-adamantanecarboxamide (13). White solid; 34.06 g (95percent); m.p. 177–179 °C(literature value, 185.5–191.7 °C [48]). 1H-NMR (DMSO-d6, 400 MHz) δ: 6.89 (brs, 1H), 6.62 (brs, 1H), 1.93 (s, 3H), 1.73–1.74 (m, 6H), 1.60–1.68 (m, 6H).3-Aminomethyl-I-adamantanol Step 1: 1-Adamantanecarboxamide: To a stirred and cooled (-10 °C) solution of adamantane-1 -carboxylic acid (5.0 g, 27.74 mmol) and triethylamine (3.61 g, 33.27 mmol) in THF (80 ml) was added ethyl chloroformate (3.65 g, 36.06 mmol) to result in a white precipitate. The mixture was stirred at the same temperature for 30 min and 30 percent NHExample B13 General procedure: Adamantane-1-carboxylic acid (7.4 g, 41 mmol) was heated to reflux with thionyl chloride (15 mL) and DMF (2 drops) for 3 h. The excess thionyl chloride was distilled off under reduced pressure and the residual traces were removed in vacuo for 15 min. The residue was dissolved in THF (20 mL) and added to aqueous ammonia (30percent, 100 mL) with ice cooling and stirring. After stirring for 1 h at ambient temperature, the precipitate was filtered off, HGeneral procedure: The solution of aminoalane reagent (prepared from 20 equiv. DIBAL-H in case of ester and lactonesubstrates or from 40 equiv. in case of carboxylic acid and amide substrates) was added to a solutionof carboxylic acid (1 eqiuv.) or its derivative (lactone, ester or amide, 1 equiv.) in anhydrous THF atroom temperature. Stirring was continued for 16 hours at 66 C. After this time, the reaction mixturewas cooled, quenched with aqueous solution of KHSO4 and the product was extracted with CHCl3.The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude product was purified by silica gel chromatography with hexane / ethyl acetateelution.

Reproduction of Sindbis virus strains sensitive and resistant to 1-adamantanecarboxamide

Molecular Weight:179.26
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:179.131014166
Monoisotopic Mass:179.131014166
Topological Polar Surface Area:43.1
Heavy Atom Count:13
Complexity:218
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes