Methanol → 1-(2'-Fluoro-3'-piperidylpropyl)-2-nitroimidazole

HRID 1651306ノート

反応式

HRID 1651306 の反応式
O[CH:2]([CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10].CCN(S(F)(F)[F:25])CC.CO>O1CCOCC1>[F:25][CH:2]([CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10]

参加物

5

反応物 3

HCID 887MethanolHCID 50981PimonidazoleHCID 123472(Diethylamino)sulfur trifluoride2 回

生成物 1

HCID 190880061-(2'-Fluoro-3'-piperidylpropyl)-2-nitroimidazole

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 2.2 g (8.65 mmol) of 1-(2'-hydroxy-3'-piperidylpropyl)-2-nitroimidazole in 20 ml of dry dioxane, 2.5 g (15.5 mmol) of DAST was dropwise added with cooling by ice and reacted for 5 hours at room temperature. After reaction, to the solution, 10 ml of methanol was added to decompose excess DAST. Then, the solution was concentrated and partitioned between chloroform and water. The pH of the aqueous phase was adjusted to 12 by the addition of an aqueous solution of sodium hydroxide and the liquid was again partitioned between chloroform and water. The chloroform phase was dried on magnesium sulfate and filtered. The filtrate was concentrated and subjected to isolation and purification by silica gel chromatography to give 1-(2'-fluoro-3'-piperidylpropyl)-2-nitroimidazole, which was treated with hydrochloric acid to form a hydrochloride and crystallized from ethanol to give 560 mg of crystalline hydrochloride of 1-(2'-fluoro-3'-piperidylpropyl)-2-nitroimidazole.

後処理

  1. temperaturewith cooling by ice
  2. customreacted for 5 hours at room temperature
  3. customAfter reaction
  4. concentrationThen, the solution was concentrated
  5. custompartitioned between chloroform and water
  6. additionThe pH of the aqueous phase was adjusted to 12 by the addition of an aqueous solution of sodium hydroxide
  7. customthe liquid was again partitioned between chloroform and water
  8. dry with materialThe chloroform phase was dried on magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated
  11. customsubjected to isolation and purification by silica gel chromatography

出典と根拠

ORDレコード
ord-eb4e492d6dad42c0a1935af87650531f
出典データセット
uspto-grants-1990_05
特許番号
US04927941

反応ノート

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