Sodium Azide → 3-Azidomethyl-2-(5-bromopyridin-3-yl)-2-azabicyclo[3.1.0]hexane

HRID 241602노트

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HRID 241602 반응식
CS(O[CH2:6][CH:7]1[CH2:12][CH:11]2[CH:9]([CH2:10]2)[N:8]1[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=1)(=O)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>CC1C=COC=1C.CCOCC>[N:20]([CH2:6][CH:7]1[CH2:12][CH:11]2[CH:9]([CH2:10]2)[N:8]1[C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=1)=[N+:21]=[N-:22]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 866749142-(5-Bromopyridin-3-yl)-2-azabicyclo[3.1.0]hex-3-ylmethyl methanesulfonate

생성물 1

HCID 711149553-Azidomethyl-2-(5-bromopyridin-3-yl)-2-azabicyclo[3.1.0]hexane수율 90%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 343372,3-Dimethylfuran용매

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온도
90 °C

실험 절차

To a stirred solution of methane sulfonate (as obtained in Step (i) of Example 1) (215 mg, 0.62 mmol) in dry dimethylfuran (2 mL) was added sodium azide (180 mg, 2.77 mmol). The reaction mixture was gradually heated to 90° C. and stirred for 16 hours. Upon completion of the reaction, it was diluted with ether, washed with water, brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by silica gel flash column chromatography to obtain the title compound as gummy liquid of 164 mg. Yield: 90%.

후처리

  1. customUpon completion of the reaction, it
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by silica gel flash column chromatography

출처 및 근거

ORD 기록
ord-787b1c2a609141ca87f2385f22b1179f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653071B2

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