Sodium Azide → cis-2-Azidocyclopentyl 4-bromophenyl ether

HRID 2060834노트

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HRID 2060834 반응식
CS(O[C@@H:6]1[CH2:10][CH2:9][CH2:8][C@H:7]1[O:11][C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C)C=O>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C@@H:7]2[CH2:8][CH2:9][CH2:10][C@@H:6]2[N:19]=[N+:20]=[N-:21])=[CH:13][CH:14]=1

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 86653037trans-2-(4-Bromophenoxy)cyclopentyl methanesulfonate

생성물 1

HCID 86653043cis-2-Azidocyclopentyl 4-bromophenyl ether

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of trans-2-(4-bromophenoxy)cyclopentyl methanesulfonate (3.52 g, 10.5 mmol) in dimethylformamide (22 mL) was added sodium azide (897 mg, 13.7 mmol) and the reaction was heated at 100° C. for 18 hours. The reaction was cooled to room temperature and partitioned between ethyl acetate and 1N aqueous lithium chloride solution. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with saturated aqueous sodium chloride solution, dried over calcium sulfate, filtered and concentrated in vacuo to provide product as a brown oil, which was used in the next step without additional purification. Yield: 2.59 g, 9.18 mmol, 87%. 1H NMR (400 MHz, CDCl3) δ 1.65-1.73 (m, 1H), 1.89-2.05 (m, 5H), 3.74 (m, 1H), 4.66 (m, 1H), 6.83 (d, J=9.0 Hz, 2H), 7.39 (d, J=9.0 Hz, 2H).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. custompartitioned between ethyl acetate and 1N aqueous lithium chloride solution
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layers were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over calcium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide product as a brown oil, which
  9. customwas used in the next step without additional purification

출처 및 근거

ORD 기록
ord-ada4ed0778d44051b5286c9a47ab4263
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278457B2

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