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

HRID 884024노트

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HRID 884024 반응식
[C:1]([N:8]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][C@H:9]1[C:18]([O:20][CH3:21])=[O:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[C:1]([N:8]1[CH2:12][C@@H:11]([N:22]=[N+:23]=[N-:24])[CH2:10][C@H:9]1[C:18]([O:20][CH3:21])=[O:19])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

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-dicarboxylate수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

Methyl (2S,4R)-1-Boc-4-[(methylsulfonyl)oxy]pyrrolidine-2-carboxylate (9 g, 27.86 mmol) obtained in Step C was dissolved in DMF (80 ml) and NaN3 (2.7 g, 41.79 mmol) was added thereto and stirred at 90° C. for 10 hours. The reaction mixture was concentrated in vacuo, extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (eluent, EtOAc/Hex=1/4) to give the title compound (6 g, 80%).

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (eluent, EtOAc/Hex=1/4)

출처 및 근거

ORD 기록
ord-7062b24380484bf88884e792a1d1f707
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236955B2

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