* 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.
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6156 - 6160
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4629 - 4639
[3] Journal of the American Chemical Society, 1972, vol. 94, p. 4628 - 4634
[4] Magnetic Resonance in Chemistry, 1990, vol. 28, # 5, p. 448 - 457
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Reference：
[1] Chemical Communications, 2010, vol. 46, # 15, p. 2674 - 2676
[2] Chemical Communications, 2010, vol. 46, # 15, p. 2674 - 2676
Stage #1: ethylmagnesium bromide With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at 20℃;
Stage #2: 2-Adamantanone In tetrahydrofuran; diethyl ether at 0℃; for 3h;
16.42 parts of the compound represented by the formula (I-88-a) and 53.29 parts of tetrahydrofuran were charged and dissolved by stirring at 23 C. To the resulting mixture, 2.44 parts of dimethylaminopyridine was added at 23 C., followed by stirring at 50 C. for 30 minutes.To the obtained mixture, a mixed solution of 18.03 parts of 2-ethyl-2-adamantanol and 54.09 parts of tetrahydrofuran was further added dropwise over 1 hour and the mixture was stirred at 50 C. for 10 hours. 30 parts of ion-exchanged water and 60 parts of ethyl acetate were added to the obtained mixture, washed, and liquid separation was performed to recover the organic layer.30 parts of ion exchanged water was added to the recovered organic layer, washed, and liquid separation was performed to recover the organic layer.This separating and washing operation was repeated three times. The recovered organic layer was concentrated and then subjected to column fractionation under the following conditions to obtain 25.62 parts of the compound represented by the formula (I-88-b).
2.31 parts of the salt represented by formula (I-1-a) and 20 parts of acetonitrile are mixed,The mixture was stirred at 23 C for 30 minutes.1.80 parts of carbonyldiimidazole was added to the obtained mixed solution,The mixture was stirred at 60 C for 2 hours.2.17 parts of the compound represented by the formula (I-27-b) was added to the obtained reaction solution, and the mixture was stirred at 60 C. for 2 hours and then cooled to 23 C. Chloroform (40 parts) and ion-exchanged water (20 parts) were added to the obtained reaction mixture, and the mixture was stirred at 23 C. for 30 minutes, then, separated, and the organic layer was taken out. 20 parts of ion-exchanged water was added to the obtained organic layer, the mixture was stirred at 23 C. for 30 minutes, and then liquid-separated to take out the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, and the concentrated mixture was applied to a column (silica gel 60N (spherical, neutral) 100-210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: n-heptane / ethyl acetate = 1/1). By fractionating, 2.18 parts of a compound represented by the formula (I-27-c) was obtained.
4.88 parts of the salt represented by the formula (I-1-a) and 25 parts of dimethylformamide were mixed and stirred at 23 C. for 30 minutes. 3.88 parts of the compound represented by the formula (I-1-b) was added to the obtained mixed solution, and the mixture was further stirred at 50 C. for 2 hours. The resulting mixed solution was added with the compound of formula (I-3By adding 3.93 parts of the compound represented by the formula (c), stirring at 50 C. for 3 hours, and cooling to 23 C.,A solution containing a salt represented by the formula (I-3-d) was obtained
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