Sodium Azide → (1R,2S)-2-azidocyclohexyl 4-bromophenyl ether

HRID 2060842ノート

反応式

HRID 2060842 の反応式
CS(O[C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[O:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O.O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C@@H:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C@@H:6]2[N:20]=[N+:21]=[N-:22])=[CH:14][CH:15]=1

参加物

5

反応物 2

HCID 33557Sodium AzideHCID 86653049(1R,2R)-2-(4-bromophenoxy)cyclohexyl methanesulfonate

生成物 1

HCID 86653050(1R,2S)-2-azidocyclohexyl 4-bromophenyl ether

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a solution of (1R,2R)-2-(4-bromophenoxy)cyclohexyl methanesulfonate (3.55 g, 10.2 mmol) in dimethylformamide (21.8 mL) and water (2.43 mL) was added sodium azide (95%, 2.09 mg, 30.5 mmol) and the reaction was heated at 120° C. for 23 hours. The reaction was cooled to room temperature, diluted with water (400 mL) and extracted with ethyl acetate (4×400 mL). The combined organic layers were washed with aqueous lithium chloride solution (1N, 400 mL), washed with water (400 mL), and dried over magnesium sulfate. Filtration and removal of solvents in vacuo afforded (1R,2S)-2-azidocyclohexyl 4-bromophenyl ether as an orange oil, which was used in the next step without additional purification. Yield: 2.85 g, 9.62 mmol, 94%. 1H NMR (400 MHz, CDCl3) δ 1.36-1.48 (m, 2H), 1.62-1.76 (m, 4H), 1.96-2.07 (m, 2H), 3.63 (m, 1H), 4.43 (m, 1H), 6.85 (d, J=9.0 Hz, 2H), 7.39 (d, J=8.9 Hz, 2H).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate (4×400 mL)
  3. washThe combined organic layers were washed with aqueous lithium chloride solution (1N, 400 mL)
  4. washwashed with water (400 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and removal of solvents in vacuo

出典と根拠

ORDレコード
ord-b133e3d5005443f3a4825f4d573684aa
出典データセット
uspto-grants-2012_10
特許番号
US08278457B2

反応ノート

読み込み中…