Styrene Oxide → 1-(2-hydroxy-2-phenyl-ethyl)-4-(6-fluoro-1-methyl-1H-indazol-3-yl)-piperidine

HRID 2260640

反応式

HRID 2260640 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[C:18]1([CH:24]2[CH2:26][O:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[OH:25][CH:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:26][N:15]1[CH2:16][CH2:17][CH:12]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[N:8]([CH3:11])[N:7]=2)[CH2:13][CH2:14]1

参加物

4

反応物 2

HCID 7276Styrene OxideHCID 140326086-Fluoro-1-methyl-3-(piperidin-4-yl)-1H-indazole

生成物 1

HCID 189988231-(2-hydroxy-2-phenyl-ethyl)-4-(6-fluoro-1-methyl-1H-indazol-3-yl)-piperidine収率 33%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-(6-fluoro-1-methyl-1H-indazol-3-yl)piperidine (1 g; 4.3 mmol) and phenyloxirane (0.6 g; 5 mmol) in 10 ml acetonitrile was refluxed for 16 h. The cooled reaction mixture was concentrated in vacuo and purified by chromatography on silica gel 60 with ethyl acetate: methanol (9:1, v/v) as eluent. Concentration of the appropriate fractions gave 500 mg (33%) of 1-(2-hydroxy-2-phenyl-ethyl)-4-(6-fluoro-1-methyl-1H -indazol-3-yl)-piperidine.

後処理

  1. temperaturewas refluxed for 16 h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. custompurified by chromatography on silica gel 60 with ethyl acetate: methanol (9:1

出典と根拠

ORDレコード
ord-57e9edea1081492480bb53605c9388f9
出典データセット
uspto-grants-1995_12
特許番号
US05478845

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