Water → 1-[2-(2-Azidomethyl-4-bromophenoxy)ethyl]pyrrolidine

HRID 734848ノート

反応式

HRID 734848 の反応式
[N-:1]=[N+:2]=[N-:3].[Na+].[Br:5][C:6]1[CH:19]=[CH:18][C:9]([O:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:8]([CH2:20]Cl)[CH:7]=1.O>CN(C=O)C>[N:1]([CH2:20][C:8]1[CH:7]=[C:6]([Br:5])[CH:19]=[CH:18][C:9]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[N+:2]=[N-:3]

参加物

5

反応物 3

HCID 962WaterHCID 33557Sodium AzideHCID 690598221-[2-(4-Bromo-2-chloromethylphenoxy)ethyl]pyrrolidine

生成物 1

HCID 860769251-[2-(2-Azidomethyl-4-bromophenoxy)ethyl]pyrrolidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
35 °C

実験手順

0.33 g (5.00 mmol) of sodium azide were added to a solution of 500 mg (1.57 mmol) of 1-[2-(4-bromo-2-chloromethylphenoxy)ethyl]pyrrolidine in 5 mL of DMF and the mixture was stirred for 16 hours at 35° C. Water was added and the phases were separated. The aqueous phase was exhaustively extracted with DCM, and the combined organic extracts were washed with saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, and evaporated down in vacuo. The crude product was used in the next reaction step without any further purification. Yield: 0.42 g (82% of theoretical); C13H17BrN4O (M=325.204); HPLC-MS: 5.62 minutes (method A).

後処理

  1. customthe phases were separated
  2. extractionThe aqueous phase was exhaustively extracted with DCM
  3. washthe combined organic extracts were washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated down in vacuo
  6. customThe crude product was used in the next reaction step without any further purification
  7. custom5.62 minutes (method A)

出典と根拠

ORDレコード
ord-feab30cb73504946a73471613e5e3b08
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

反応ノート

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