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

HRID 859886ノート

反応式

HRID 859886 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

(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).

後処理

  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)

出典と根拠

ORDレコード
ord-50c4b5c20d9740fd99ed0104f67416e4
出典データセット
uspto-grants-2006_12
特許番号
US07153851B2

反応ノート

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