content_image/921432.jpg content_image/921434.jpg content_image/921437.jpg content_image/921435.jpg content_image/921440.jpg content_image/921433.jpg content_image/921438.jpg content_image/921439.jpg content_image/921441.jpg
acetone, and the precipitate was collected by filtration and dried, thereby obtaining 184.5 g ofa compound (11) in the form of a white solid (purity: 88.9%, yield: 95.5% ). 

[Chemical Formula 66] 

<img src='content_image/921432.jpg'>

[0585] Subsequently, 56.2 g of the compound (11) and 562.2 g of acetonitrile were prepared, and 77.4 g of p-tolu› enesulfonic acid monohydrate was added thereto. The result› ant was refluxed at 110° C. for 3 hours. Then, the reaction mixture was filtered, and the filtrate was concentrated and dried to obtain a solid. 900 g oft-butyl methyl ether was added to the obtained solid and stirred. Thereafter, the resultant was filtered, and the residue was dried, thereby obtaining 22.2 g of a compound (12) in the form of a white solid (purity: 91.0%, yield: 44.9%). 

[Chemical Formula 67] 

<img src='content_image/921434.jpg'>

[0586] Subsequently, 4.34 g of the compound (12) (purity: 94.1 %), 3.14 g of 2-benzyloxyethanol and 43.4 g of toluene were prepared, and 0.4 7 g of p-toluenesulfonic acid monohy› drate was added thereto. The resultant was refluxed at 105° C. for 20 hours. Then, the reaction mixture was filtered, and 20 g of hexane was added to the residue and stirred. Thereafter, the resultant was filtered, and the residue was dried, thereby obtaining 1.41 g ofa compound (13) (yield: 43.1%). 

[Chemical Formula 68] 

<img src='content_image/921437.jpg'>

<img src='content_image/921435.jpg'>

<img src='content_image/921440.jpg'>

[0587] The obtained compound (13) was analyzed by NMR. 

[0588] $^{1}$H-NMR (DMSO-d6, 400 MHz): Ii (ppm)=4.74-4. 83 (t, lH, OH), 4.18-4.22 (t, 2H, Ha),3.59-3.64 (q, 2H, H 6 ) 

[0589] $^{19}$F-NMR (DMSO-d6, 376 MHz): Ii (ppm)=-106.6 

[0590] From the results shown above, it was confirmed that the compound (13) bad a structure shown below. 

[Chemical Formula 69] 

<img src='content_image/921433.jpg'>

[0591] Next, 1.00 g of the compound (13) and 3.00 g of acetonitrile were prepared, and 0.82 g of 1-adamantanecar› bonyl chloride and 0.397 g of triethylamine were dropwise added thereto while cooling with ice. Then, the resultant was stirred at room temperature for 20 hours, followed by filtra› tion. The filtrate was concentrated and dried, and dissolved in 30 g of dichloromethane, followed by washing with water three times. Thereafter, the organic phase was concentrated and dried, thereby obtaining 0.82 g of a compound (14) (yield: 41%). 

[Chemical Formula 70] 

<img src='content_image/921438.jpg'>

<img src='content_image/921439.jpg'>

-continued 

<img src='content_image/921441.jpg'>

