2-(Trifluoromethyl)oxirane → 3-((3-Phenoxyphenyl)((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)amino)-1,1,1-trifluoro-2-propanol

HRID 644958

反応式

HRID 644958 の反応式
[O:1]([C:8]1[CH:9]=[C:10]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])[CH:17]=2)[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]([F:35])([F:34])[CH:31]1[O:33][CH2:32]1.FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C.O.C(OCC)(=O)C>[O:1]([C:8]1[CH:9]=[C:10]([N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:27])([F:28])[CH:24]([F:25])[F:26])[CH:17]=2)[CH2:32][CH:31]([OH:33])[C:30]([F:35])([F:34])[F:29])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 3

HCID 5207692-(Trifluoromethyl)oxiraneHCID 2733225Ytterbium triflateHCID 10548476N-(3-phenoxyphenyl)-[[3-(1,1,2,2-tetrafluoroethoxy) phenyl]methyl]amine

生成物 1

HCID 98707043-((3-Phenoxyphenyl)((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)amino)-1,1,1-trifluoro-2-propanol収率 62.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a mixture of the amine product (15.0 g, 0.038 mol) from EX-1B and 1,1,1-trifluoro-2,3-epoxypropane (8.58 g, 0.077 mol, TCI) was added a suspension of ytterbium (III) trifluoromethanesulfonate (2.37 g, 0.0031 mol) in 15 mL of acetonitrile. The resulting mixture was heated at 50° C. in a sealed glass vial for 1.5 h. The reaction mixture was cooled to room temperature then diluted with water and ethyl acetate and extracted. The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with 1:4 ethyl acetate in hexane to afford 12.03 g (62%) of the desired (2RS)-3-[(3-phenoxyphenyl)[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol product as a yellow oil. Anal. calcd. for C24H20F7NO3: C, 57.26; H, 4.00; N, 2.78. Found: C, 56.96; H, 4.35; N, 2.69. HRMS calcd. 504.1410 [M+H]+, found: 504.1431. 1H NMR (CDCl3) δ 7.28 (m, 4H), 7.14 (t, 1H), 7.07, (m, 3H), 7.00 (s, 1H), 6.94 (d, 2H), 6.46 (dd, 1H), 6.38 (dd, 1H), 6.35 (t, 1H), 5.84 (t, 1H), 4.60 (t, 2H), 4.36 (m, 1H), 3.82 (d, 1H), 3.48 (m, 1H), 2.51 (s, 1H). 19F NMR (CDCl3) δ −79.0 (s, 3F), −88.21 (d, 2F), −137.05 (dd, 2F).

後処理

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel eluting with 1:4 ethyl acetate in hexane

出典と根拠

ORDレコード
ord-7d96b00c4c4b441a89904712476cb1dc
出典データセット
uspto-grants-2010_04
特許番号
US07700658B2

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