3-Hydroxy-1-adamantyl methacrylate

1.79 parts of the compound represented by the formula (I-6-d) and 20 parts of acetonitrile are mixed, and the mixture is stirred at 23 C. for 30 minutes, and then 1.34 of the compound represented by the formula (I-1-e) is mixed. Then, the mixture was heated to 50 C., and then stirred at 50 C. for 2 hours. To the obtained mixture, 2.48 parts of the compound represented by the formula (I-1-c) was added, and the mixture was stirred at 50 C. for 2 hours. After cooling the obtained mixture to 23 C., 50 parts of chloroform and 20 parts of ion-exchanged water were added, and the mixture was stirred at 23 C. for 30 minutes.After separating, the organic layer was taken out. 20 parts of ion-exchanged water was added to the obtained organic layer, and the mixture was stirred at 23 C. for 30 minutes, and then separated to take out the organic layer. This washing operation was repeated five times. The obtained organic layer is concentrated, and the concentrated mixture is passed through a column (silica gel 60N (spherical, neutral)).The compound 2.21 represented by the formula (IA-6-f) was obtained by fractionation using 100-210 mum; developing solvent: n-heptane / ethyl acetate = 1/2, manufactured by Kanto Chemical Co., Ltd. Got a part. 1.50 parts of the obtained compound represented by the formula (IA-6-f), 0.01 part of sulfuric acid and 20 parts of acetonitrile were mixed, and the mixture was stirred at 23 C. for 6 hours. The obtained mixture was concentrated to obtain 1.22 parts of a compound represented by the formula (IA-6-g).1.79 parts of a compound represented by the formula (I-6-d) and 20 parts of acetonitrile were mixed, and the mixture was stirred at 23 C for 30 minutes. And 1.34 parts of a compound represented by the formula (I-1-e) were added, and the mixture was heated to 50 C. and stirred at 50 C. for 2 hours. To the obtained mixture, 2.48 parts of the compound represented by the formula (I-1-c) was added, and the mixture was stirred at 50 C. for 2 hours. After the obtained mixture was cooled to 23 C., 50 parts of chloroform and 20 parts of ion-exchanged water were added, and the mixture was stirred at 23 C. for 30 minutes. 20 parts of ion-exchanged water was added to the obtained organic layer, and the mixture was stirred at 23 C. for 30 minutes, and then separated to take out the organic layer. This washing operation was repeated five times. The obtained organic layer was concentrated, and the concentrated mixture was subjected to column chromatography (silica gel 60N (spherical, neutral) 100 to 210 mum; Kanto Chemical Co., Ltd., developing solvent: n-heptane / ethyl acetate = 1/2). By fractionation, 2.21 parts of a compound represented by the formula (IA-6-f) was obtained. 1.50 parts of the obtained compound represented by the formula (IA-6-f), 0.01 part of sulfuric acid and 20 parts of acetonitrile were mixed, and the mixture was stirred at 23 C. for 6 hours.The obtained mixture was concentrated to obtain 1.22 parts of a compound represented by the formula (IA-6-g).1.79 parts of the compound represented by the formula (I-6-d) and 20 parts of acetonitrile are mixed, and the mixture is stirred at 23 C. for 30 minutes, and then 1.34 of the compound represented by the formula (I-1-e) is mixed. Then, the mixture was heated to 50 C., and then stirred at 50 C. for 2 hours. 1.24 parts of the compound represented by the formula (I-1-c) was added to the obtained mixture, and the mixture was stirred at 50 C. for 2 hours. Cool the resulting mixture to 23 CAfter the reaction, 50 parts of chloroform and 20 parts of ion-exchanged water were added, and the mixture was stirred at 23 C. for 30 minutes. 20 parts of ion-exchanged water was added to the obtained organic layer, and the mixture was stirred at 23 C. for 30 minutes, and then separated to take out the organic layer. This washing operation was repeated five times. The obtained organic layer was concentrated, and the concentrated mixture was subjected to column chromatography (silica gel 60N (spherical, neutral) 100 to 210 mum; Kanto Chemical Co., Ltd., developing solvent: n-heptane / ethyl acetate = 1/1). By fractionation, 1.09 parts of a compound represented by the formula (IB-6-f) were obtained.. 1.05 part of the obtained compound represented by the formula (IB-6-f), 0.01 part of sulfuric acid and 20 parts of acetonitrile were mixed and stirred at 23 C for 6 hours. The obtained mixture was concentrated to obtain 0.92 parts of a compound represented by the formula (IB-6-g).1.79 parts of a compound represented by the formula (I-6-d) and 20 parts of acetonitrile were mixed, and the mixture was stirred at 23 C for 30 minutes. And 1.34 parts of a compound represented by the formula (I-1-e) were added, and the mixture was heated to 50 C. and stirred at 50 C. for 2 hours. 1.24 parts of the compound represented by the formula (I-1-c) was added to the obtained mixture, and the mixture was stirred at 50 C. for 2 hours. After the obtained mixture was cooled to 23 C., 50 parts of chloroform and 20 parts of ion-exchanged water were added, and the mixture was stirred at 23 C. for 30 minutes. 20 parts of ion-exchanged water was added to the obtained organic layer, and the mixture was stirred at 23 C. for 30 minutes, and then separated to take out the organic layer. This washing operation was repeated five times. The obtained organic layer was concentrated, and the concentrated mixture was subjected to column chromatography (silica gel 60N (spherical, neutral) 100 to 210 mum; Kanto Chemical Co., Ltd., developing solvent: n-heptane / ethyl acetate = 1/1). By fractionation, 1.09 parts of a compound represented by the formula (IB-6-f) were obtained. 1.05 part of the obtained compound represented by the formula (IB-6-f), 0.01 part of sulfuric acid and 20 parts of acetonitrile were mixed and stirred at 23 C for 6 hours. By concentrating the obtained mixture, 0.92 parts of a compound represented by the formula (IB-6-g) was obtained.30 parts of the compound represented by the formula (I-1-a), 120 parts of chloroform and 18.6 parts of dimethylaminopyridine were charged and stirred at 23 C. for 30 minutes. To the resulting mixture, 13.9 parts of a compound represented by the formula (I-1-b) was added, and the mixture was stirred at 60 C. for 6 hours. The obtained reaction product was cooled to 23 C. Thereafter, 50 parts of 1% hydrochloric acid was added, and the mixture was stirred at 23 C. for 30 minutes, and the mixture was allowed to stand and liquid separation. To the recovered organic layer, 25 parts of a 10% potassium carbonate aqueous solution was added and the mixture was stirred at 23 C. for 30 minutes, and the mixture was allowed to stand and liquid separation to recover the organic layer. 50 parts of ion-exchanged water was added to the recovered organic layer, and the mixture was stirred at 23 C. for 30 minutes, and the mixture was allowed to stand still and the organic layer was washed with water. This washing operation was repeated four times. The organic layer washed with water was concentrated, and the concentrated mass was applied to a column(Kanto chemical silica gel 60 N (spherical, neutral) 100-210 mum developing solvent: n-heptane / ethyl acetate = 5/1) to obtain 15.0 parts of the compound represented by the formula (I-1) Obtained.20 parts of the compound represented by the formula (I-9-a) and 240 parts of chloroform were mixed and stirred at 23 C. for 30 minutes.15.1 parts of a compound represented by the formula (I-9-b) was added to the obtained mixture, and the mixture was stirred at 60 C. for 12 hours.To the resulting mixture, 60 parts of ion-exchanged water was added, after stirring for 30 minutes, the organic layer was recovered by liquid separation.This washing operation was carried out six times. The collected organic layer was concentrated to obtain 27 parts of the compound represented by the formula (I-9-c).3.19 parts of the compound represented by the formula (I-68-a) and 20 parts of methylene chloride were mixed. 1.09 part of the compound represented by the formula (I-2-f) was charged in the obtained mixture, and the mixture was stirred at 40C for 3 hours. The resulting mixture was cooled to 23C and further stirred for 30 minutes and then filtered. The obtained filtrate was concentrated to obtain 3.67 parts of a compound represented by the formula (I-68-b).20 parts of the compound represented by the formula (I-4-a) and 240 parts of chloroform were mixed and stirred at 23 C. for 30 minutes.15.1 parts of the compound represented by the formula (I-4-b) was added to the obtained mixture, and the mixture was stirred at 60 C. for 12 hours.To the resulting mixture, 60 parts of ion-exchanged water was added, after stirring for 30 minutes, the organic layer was recovered by liquid separation.This washing operation was carried out six times.The collected organic layer was concentrated to obtain 27 parts of the compound represented by the formula (I-4-c).Synthesis of Monomer 1 (0219) (0220) In 200 ml of acetonitrile, 50.0 g of Starting Monomer 1 was mixed with 34.3 g of triethylamine and 0.05 g of 2, 2?-methylenebis(6-t-butyl-p-cresol). To the mixture below 20 C., 36.3 g of methyl 1-chloro-2-methylpropyl ether was added dropwise, followed by stirring at room temperature for 4 hours. 300 ml of water was added to quench the reaction, followed by standard workup. Purification by distillation gave 62.2 g (yield 91%) of the end compound. (0221) Boiling point: 110-111 C./15 Pa (0222) 1H-NMR (600 MHz in DMSO-d6): delta=0.80 (6H, dd), 1.48 (2H, s), 1.64-1.75 (4H, m), 1.77 (1H, sept), 1.81 (3H, s), 1.94-2.04 (4H, m), 2.09 (2H, app dt), 2.26 (2H, t), 3.10 (3H, s), 4.42 (1H, d), 5.59 (1H, m), 5.92 (1H, s) ppmTo a mixture of 20 parts of the compound represented by formula (I-13-a), made by Idemitsu Kosan Co., Ltd., and 60 parts of chloroform, 21.2 parts of 50% aqueous 4-methylmorpholine N-oxide solution and 1.5 parts of 4% aqueous osmium tetraoxide solution were added. The resulting mixture was stirred at room temperature for 18 hours. To the resulting reaction mixture, 153 parts of 5% aqueous oxalic acid solution was added thereto and extracted with ethyl acetate, followed by separating into an organic layer. The organic layer was washed with deionized water, followed by concentrating it with decompression to obtain 13.2 parts of the compound represented by formula (I-13-b). 1H-NMR (DMSO-d6): delta=5.0-4.8 (1H, m), 4.8-4.5 (2H, brm), 3.5-3.3 (2H, m), 2.3-2.2 (2H, m), 2.0-1.8 (6H, m), 1.4-1.6 (6H, m), 1.2 (3H, s)Example 4 Synthesis of (2-oxo-2-(3-(2, 2, 2-trifluoroacetoxy)-1-adamantyloxy)ethyl methacrylate After a reaction vessel which had been sufficiently dried inside by vacuum heating was replaced with dry nitrogen, 29.43 g (0.1 mol) of

Molecular Weight:236.31
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:236.14124450
Monoisotopic Mass:236.14124450
Topological Polar Surface Area:46.5
Heavy Atom Count:17
Complexity:371
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes