Sodium hydride → 4-(2-(4-Fluorophenylthio)eth-1-yl)-1-tert-butoxycarbonylpiperidine

HRID 278233

反応式

HRID 278233 の反応式
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.I[CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1>O1CCCC1.CCOCC>[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:18][CH2:19]2)=[CH:6][CH:5]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 677894-FluorothiophenolHCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

生成物 1

HCID 181874814-(2-(4-Fluorophenylthio)eth-1-yl)-1-tert-butoxycarbonylpiperidine収率 95.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a slurry of sodium hydride (47 mg, 60% in mineral oil, 1.2 mmol) in tetrahydrofuran at 0° C. was added 4-fluorothiophenol (0.1 mL, 0.94 mmol). The reaction mixture was warmed to rt. for 20 min, followed by addition of 4-(2-iodoeth-1-yl)-1-tert-butoxycarbonylpiperidine (265 mg, 0.78 mmol, from Step C). The reaction was then heated to reflux for 10 min, cooled and diluted with ether. The organic layer was washed with 1 N NaOH, dried over magnesium sulfate and concentrated to provide 252 mg (95%) of the title compound. ESI-MS: 340.0 (M+H); HPLC A: 4.07 min.

後処理

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 10 min
  3. temperaturecooled
  4. washThe organic layer was washed with 1 N NaOH
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-49df08d0eac44a448646ced71f211cad
出典データセット
uspto-grants-2002_03
特許番号
US06358979B1

関連ノート

読み込み中…