Water → 4-Azido-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

HRID 1071503노트

반응식

HRID 1071503 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11](OS(C)(=O)=O)[CH2:10][CH:9]1[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+].O.CCCCCC.C(OCC)(=O)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([N:19]=[N+:20]=[N-:21])[CH2:10][CH:9]1[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 33557Sodium AzideHCID 197903964-Methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl EsterHCID 21226206Ethyl acetate hexane

생성물 1

HCID 140411954-Azido-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

The 4-methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester (135.21 mg, 0.48 mmol) was taken up in dry DMF under argon and sodium azide (156.00 mg, 2.40 mmol) was added. The reaction was then heated to 60° C. for 48 h. The reaction was poured into water and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with sat NaHCO3 and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (5:1 hexane-ethyl acetate) Yield 93.41 mg.

후처리

  1. extractionthe aqueous layer was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with sat NaHCO3 and brine
  3. dry with materialthen dried over MgSO4
  4. filtrationThe solution was filtered
  5. customthe solvent removed under reduced pressure
  6. customThe product was isolated by flash chromatography

출처 및 근거

ORD 기록
ord-f5b78fb38d1c45b3b62efda05b70320a
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906067B2

반응 노트

불러오는 중…