Jan. 13, 2011  88  US 2011/0008728 Al  -continued  [1150]  The obtained compound (IV) was analyzed by  NMR.  [1151]  $^{1}$H-NMR (DMSO-d6, 400 MHz):  Ii  (ppm)=8.81 (s,  lH, ff), 4.37-4.44 (t, 2H,  Hd),  4.17-4.26 (t, 2H, ff), 3.03-3.  15 (q, 6H, H 6 ),  1.61-1.98 (m, 15H, Adamantane), 1.10-1.24  (t, 9H,  Ha)  [1152]  $^{19}$F-NMR (DMSO-d6, 376 MHz):  Ii  (ppm)=-106.  61  [1153]  From the results above, it was confirmed that the  compound (IV) had a structure shown below.  [1145]  $^{1}$H-NMR (DMSO-d6, 400 MHz):  Ii  (ppm)=4.74-4.  83 (t, 1H$_{2}$OH), 4.18-4.22 (t, 2H,  Ha),  3.59-3.64 (q, 2H, H 6 )  [1146]  $^{19}$F-NMR (DMSO-d6, 376 MHz):  Ii  (ppm)=-106.6  [1147]  From the results shown above, it was confirmed that  the compound (III) had a structure shown below.  [Chemical Formula 106]  [Chemical Formula 108]  [1148]  (ii) Synthesis of Compound (IV)  [1149]  To 1.00 g of the compound (III) and 3.00 g of aceto› nitrile were dropwise added 0.82 g of 1-adamantanecarbonyl  chloride and 0.397 g oftriethylamine while cooling with ice.  Then, the resultant was stirred at room temperature for 20  hours, followed by filtration. 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 (IV) (yield: 41 % ).  [1154]  (iii) Synthesis of Compound (VI)  [1155]  4 g of the compound (V) was dissolved in 79.8 g of  dichloromethane. After confirming that the compound (VI)  had dissolved in dichloromethane, 6.87 g of potassium car› bonate was added thereto, and 3.42 g of methyl adamantyl  bromoacetate was further added. A reaction was effected  under reflux for 24 hours, followed by filtration, washing with  water, and crystallization with hexane. The resulting powder  was dried under reduced pressure, thereby obtaining 3 .98 g of  an objective compound (VI) (yield: 66%).  [1156]  The obtained compound (VI) was analyzed by  NMR.  [1157]  $^{1}$H-NMR (CDC1$_{3}$ ,  400 MHz):  Ii  (ppm)=7.83-7.86  (m, 4H, Phenyl), 7.69-7.78 (m, 6H, Phenyl), 7.51 (s, 2H,  Hd),  4.46 (s, 2H, ff), 2.39 (s, 6H,  Ha),  2.33 (s, 2H, Adamantane ),  2.17 (s, 2H,Adamantane), 1.71-1.98 (m, llH,Adamantane),  1.68 (s, 3H, H 6 ),  1.57-1.61 (m, 2H, Adamantane)  [1158]  From the results above, it was confirmed that the  compound (VI) had a structure shown below.  (II)  (III)  [1144]  The obtained compound (III) was analyzed by  NMR.  (IV)  -continued  (III)  [Chemical Formula 107] 