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

HRID 2060842노트

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HRID 2060842 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b133e3d5005443f3a4825f4d573684aa
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278457B2

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