Sodium Azide → (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine

HRID 2108780노트

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HRID 2108780 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH2:16]OS(C)(=O)=O)[C@@H:13]([OH:22])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C)C=O>[N:23]([CH2:16][C@@H:14]1[C@@H:13]([OH:22])[CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:15]1)=[N+:24]=[N-:25]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 86600235(3R,4R)-1-benzyloxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidine

생성물 1

HCID 86600232(3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine수율 86.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

(3R,4R)-1-Benzyloxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidine (125 mg) was then dissolved in N,N-dimethylformamide (3 mL) and sodium azide (50.0 mg) was added. The mixture was stirred at 100° C. for 1 hour and was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (5 mL). The solution was then washed with water (2×1 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: ethyl acetate) to give (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine as a milky white syrup (91.0 mg). This compound was identical to the compound obtained by Process A.

후처리

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (5 mL)
  3. washThe solution was then washed with water (2×1 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluant: ethyl acetate)

출처 및 근거

ORD 기록
ord-d636fbd4ffb7468bb5d52fd8c8e156de
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514451B2

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