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

HRID 241602ノート

反応式

HRID 241602 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 343372,3-Dimethylfuran溶媒

反応条件

温度
90 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-787b1c2a609141ca87f2385f22b1179f
出典データセット
uspto-grants-2014_02
特許番号
US08653071B2

反応ノート

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