Sodium Iodide → Tert-butyl[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]carbamate

HRID 546667ノート

反応式

HRID 546667 の反応式
[I-].[Na+].[H-].[Na+].N1(O[CH2:15][CH2:16][CH2:17][CH:18]([C:30]2[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=2)[C:19]([NH:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])C2C=CC=CC=2N=N1.O.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:26]([O:25][C:23](=[O:24])[NH:22][N:21]1[CH2:15][CH2:16][CH2:17][CH:18]([C:30]2[CH:35]=[C:34]([F:36])[C:33]([F:37])=[C:32]([F:38])[CH:31]=2)[C:19]1=[O:20])([CH3:29])([CH3:28])[CH3:27]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 66839387tert-butyl N'-[5-(benzotriazol-1-yloxy)-2-(3,4,5-trifluorophenyl)pentanoyl]hydrazinecarboxylateHCID 86585896Sodium bicarbonate water

生成物 1

HCID 86628505Tert-butyl[2-oxo-3-(3,4,5-trifluorophenyl)piperidin-1-yl]carbamate収率 44.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Sodium iodide (131 mg) and sodium hydride (containing 40% of mineral oil, 70 mg) were added to a solution of tert-butyl N′-[5-(benzotriazol-1-yloxy)-2-(3,4,5-trifluorophenyl)pentanoyl]hydrazinecarboxylate (420 mg) in DMF (3 mL), and the reaction solution was stirred at 100° C. for 19 hours. The reaction solution was left to cool to room temperature. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane→ethyl acetate) to obtain 134 mg of the title compound. The property values of the compound are as follows.

後処理

  1. waitThe reaction solution was left
  2. temperatureto cool to room temperature
  3. customthe organic layer was separated
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane→ethyl acetate)

出典と根拠

ORDレコード
ord-9e99ec1063f24cc382f7b2d2b6c4ba5d
出典データセット
uspto-grants-2011_05
特許番号
US07935815B2

反応ノート

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