Sodium hydride → Tert-butyl 4-[2-(2-iodo-4-nitrophenoxy)ethyl]piperidine-1-carboxylate

HRID 542005

反応式

HRID 542005 の反応式
[H-].[Na+].[OH:3][CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=1[I:29]>O1CCCC1>[I:29][C:21]1[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:20]=1[O:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidineHCID 105397331-Fluoro-2-iodo-4-nitrobenzene

生成物 1

HCID 57962636Tert-butyl 4-[2-(2-iodo-4-nitrophenoxy)ethyl]piperidine-1-carboxylate収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of sodium hydride (0.16 g, 3.9 mmol) in tetrahydrofuran (10 mL) at 0° C. was treated with a solution of tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (0.82 mL, 3.7 mmol) in tetrahydrofuran (5 mL) and stirred at 0° C. for 30 minutes. The reaction mixture was treated with a solution of 1-fluoro-2-iodo-4-nitrobenzene (1.0 g, 3.7 mmol) in tetrahydrofuran (5 mL) and heated at 70° C. for 16 h. The reaction mixture was concentrated, diluted with ethyl acetate, and washed with water. The aqueous layer was separated and extracted with additional ethyl acetate. The combined organic extracts were washed with brine, dried with sodium sulfate, filtered, and concentrated to a crude brown oil. Purification by flash column chromatography gave the desired product (1.4 g, 81%) as a yellow oil. LCMS for C18H251N2O5Na (M+Na)+: m/z=499.0.

後処理

  1. temperatureheated at 70° C. for 16 h
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. customThe aqueous layer was separated
  6. extractionextracted with additional ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to a crude brown oil
  11. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-f3958cb0ed554b0182c77a915e97325f
出典データセット
uspto-grants-2014_10
特許番号
US08871753B2

関連ノート

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