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

HRID 859886노트

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HRID 859886 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 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 then concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (5 mL) and the solution was washed with water (2×1 mL), followed by drying over anhydrous sodium sulfate and concentration under reduced pressure. The resulting residue was purified on a silica gel column (eluant=ethyl acetate) to give 91.0 mg of (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-hydroxypyrrolidine as a milky white syrup-like product. The compound was identical to the compound obtained by Process (A).

후처리

  1. concentrationwas then concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (5 mL)
  3. washthe solution was washed with water (2×1 mL)
  4. dry with materialby drying over anhydrous sodium sulfate and concentration under reduced pressure
  5. customThe resulting residue was purified on a silica gel column (eluant=ethyl acetate)

출처 및 근거

ORD 기록
ord-50c4b5c20d9740fd99ed0104f67416e4
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153851B2

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