Vinyl Acetate → 5,6-Dihydroxy-2-vinyl-2-azabicyclo[2.2.1]heptan-3-one

HRID 219518

반응식

HRID 219518 반응식
[OH:1][CH:2]1[CH:7]([OH:8])[CH:6]2[CH2:9][CH:3]1[C:4](=[O:10])[NH:5]2.[CH:11]12CC(C=[CH:16]1)C(=O)N2.S(=O)(O)[O-].[Na+].C(OC=C)(=O)C>N1C=CC=CC=1.O.[Os](=O)(=O)(=O)=O.[Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl>[OH:1][CH:2]1[CH:7]([OH:8])[CH:6]2[CH2:9][CH:3]1[C:4](=[O:10])[N:5]2[CH:11]=[CH2:16]

참가 물질

9

반응물 4

HCID 7904Vinyl AcetateHCID 4351255,6-Dihydroxy-2-azabicyclo[2.2.1]heptan-3-oneHCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-oneHCID 23665763Sodium Bisulfite

생성물 1

HCID 600076445,6-Dihydroxy-2-vinyl-2-azabicyclo[2.2.1]heptan-3-one

시약·촉매·용매 4

HCID 30318Osmium Tetroxide촉매HCID 178479786HCID 178479786, 화합물촉매HCID 962Water용매HCID 1049Pyridine용매2회

실험 절차

The intermediate 5,6-dihydroxy-2-azabicyclo[2.2.1]heptan-3-one is made by stirring a solution of 2-azabicyclo[2.2.1]hept-5-en-3-one (1.00 g, 9.16 mmole) and osmium tetroxide (2.33 g, 9.16 mmole) in pyridine (35 ml) at room temperature for 2 hours. The osmate ester is cleaved by mixing the reaction solution with a solution of sodium bisulfite (4.2 g) in water (70 ml) and pyridine (50 ml). The product is extracted from the reaction solution with 3-150 ml portions of methylene chloride. Evaporation of the dried methylene chloride gives the crude dihydroxy bicyclic amide (intermediate). The intermediate is mixed with sodium tetrachloropalladate (30 mg, 0.10 mmole) and vinyl acetate (6 ml, 66 mmole). The mixture is then refluxed for 5 days. The crude product (Compound 7) is isolated by filtration to remove the catalyst and evaporation of the excess vinyl acetate.

후처리

  1. extractionThe product is extracted from the reaction solution with 3-150 ml portions of methylene chloride
  2. customEvaporation of the dried methylene chloride
  3. customgives the crude dihydroxy bicyclic amide (intermediate)
  4. temperatureThe mixture is then refluxed for 5 days

출처 및 근거

ORD 기록
ord-657c720571d64ad8add6a04c6d205486
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202833B2

연결된 노트

불러오는 중…