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

HRID 734848노트

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HRID 734848 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
35 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-feab30cb73504946a73471613e5e3b08
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592358B2

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