Sodium hydride → (R)-6-fluoro-3-(3-oxiranylmethoxy-phenyl)-benzo[d]isoxazole

HRID 852082ノート

反応式

HRID 852082 の反応式
[H-].[Na+].CC1C=CC(S(O[CH2:14][C@@H:15]2[O:17][CH2:16]2)(=O)=O)=CC=1.[F:18][C:19]1[CH:34]=[CH:33][C:22]2[C:23]([C:26]3[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=3)=[N:24][O:25][C:21]=2[CH:20]=1>CN(C)C=O.O>[F:18][C:19]1[CH:34]=[CH:33][C:22]2[C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH2:14][C@H:15]4[CH2:16][O:17]4)[CH:27]=3)=[N:24][O:25][C:21]=2[CH:20]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 154187Glycidyl tosylate, (R)-HCID 179062783-(6-Fluoro-benzo[d]isoxazol-3-yl)-phenol

生成物 1

HCID 58928264(R)-6-fluoro-3-(3-oxiranylmethoxy-phenyl)-benzo[d]isoxazole収率 75%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

The title compound is prepared from a mixture of sodium hydride in dimethylformamide, 3-(6-fluoro-benzo[d]isoxazol-3-yl)-phenol in dimethylformamide and (2R)-(−)-glycidyl tosylate in dimethylformamide essentially as described above except that the reaction mixture is diluted with water, extracted with ethyl acetate, washed with water (twice), dried (MgSO4), concentrated and purified by column (silica) chromatography eluting with a graded solvent mixtures of toluene to 1% ether in toluene to give the title compound as a white solid (9.29 g, 75% Yield). NMR and microanalysis (C, H, N) are consistent with the final, desired compound. Chiral HPLC, 16.92 minutes, [Chiralcel OD (250×4.6 mm), 98:2 heptane/ethanol @ 0.8 mL/min, UV @ 285 nm, 18.14] shows the title compound as 95.5% e.e. mp=84-85° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with water (twice),
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by column (silica) chromatography
  6. washeluting with a graded solvent mixtures of toluene to 1% ether in toluene

出典と根拠

ORDレコード
ord-f56359d30b3d4c5ea6c7af588a836c59
出典データセット
uspto-grants-2007_08
特許番号
US07253165B2

反応ノート

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