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

HRID 2060834ノート

反応式

HRID 2060834 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 86653043cis-2-Azidocyclopentyl 4-bromophenyl ether

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ada4ed0778d44051b5286c9a47ab4263
出典データセット
uspto-grants-2012_10
特許番号
US08278457B2

反応ノート

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