Ammonium Chloride → (2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine

HRID 1090506노트

반응식

HRID 1090506 반응식
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3].[Cl-].[NH4+].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C)C=O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([N:21]=[N+:22]=[N-:23])[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3]

참가 물질

7

반응물 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18639172(2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

생성물 1

HCID 57320993(2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

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온도
75 °C

실험 절차

To a solution of (2S,4R)-1-allyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (20.0 g) in N,N-dimethylformamide (200 ml) were added ammonium chloride (5.74 g) and sodium azide (6.98 g). The resulting mixture was heated at 75° C. for 8 hours. After cooling, the mixture was diluted with ethyl acetate (1 l) and aqueous sodium hydrogen carbonate (1 l). The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo to give (2S,4S)-1-allyloxycarbonyl-4-azido-2-hydroxymethylpyrrolidine.

후처리

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-897b8bc684d34bdab13bb3900cec9b4d
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05081237

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