Sodium Azide → (2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

HRID 425126노트

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HRID 425126 반응식
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8](OS(C)(=O)=O)[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4].[N-:22]=[N+:23]=[N-:24].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([N:22]=[N+:23]=[N-:24])[CH2:7][N:6]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:4]

참가 물질

4

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HCID 33557Sodium AzideHCID 147726821-tert-Butyl 2-methyl (2S,4R)-4-((methanesulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

생성물 1

HCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
90 °C

실험 절차

(2S,4R)-4-Methanesulfonyloxypyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-methyl ester (11.9 g, 37 mmol) and NaN3 (2 equiv) were mixed in DMSO (160 mL) and stirred at 90° C. for 16 hours. The mixture was cooled then partitioned between water (200 mL) and EtOAc (400 mL). The aqueous layer was discarded, the organics washed with water (200 mL) and saturated aqueous NaCl (200 mL), then dried over Na2SO4. The solvent was evaporated to afford the title compound (8.5 g, 31 mmol), which was used without further purification. MS m/z: [M+H]+ calcd for C11H18N4O4, 270.3. found 271.3.

후처리

  1. temperatureThe mixture was cooled
  2. customthen partitioned between water (200 mL) and EtOAc (400 mL)
  3. washthe organics washed with water (200 mL) and saturated aqueous NaCl (200 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-50dd886b58bc4cf3b5714c8a7f205117
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106082B2

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