6(5H)-Phenanthridinone → 5,6-Dihydrophenanthridine

HRID 390133

반응식

HRID 390133 반응식
[CH:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=O)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1>C1COCC1>[CH:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

참가 물질

3

반응물 1

HCID 18536(5H)-Phenanthridinone

생성물 1

HCID 2199665,6-Dihydrophenanthridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The 5,6-dihydro-phenanthridine (1k) was prepared using the following procedure: Into a 500 mL round bottom flask equipped with a magnetic stir bar and a reflux condensor was placed 6(5H)-Phenanthridinone (1000 mg, 5123 μmol), THF (250 mL) (fine suspension). The flask is sparged with nitrogen, 2M BH3-dimethylsulfide complex in THF (10 mL) is added. This is allowed to stir at reflux for 24 hours. TLC shows reaction still incomplete (1/1, ethyl acetate/heptane). Solvents removed under reduced pressure. Water (50 mL) and ethyl acetate (100 mL) added. The aqueous layer is separated with ethyl acetate (3×100 mL). The organic layers are combined, dried (sodium sulfate), solids removed by filtration, and the solvents removed under reduced pressure. This is purified by silica column chromatography using heptane to 50% ethylacetate in heptane. The best fractions are pooled and the solvents are removed under reduced pressure to afford an off-white solid (270 mg, Yield: 29%). LC-MS shows mass 182 (M+H)+.

후처리

  1. customInto a 500 mL round bottom flask equipped with a magnetic stir bar
  2. customThe flask is sparged with nitrogen, 2M BH3-dimethylsulfide complex in THF (10 mL)
  3. additionis added
  4. temperatureat reflux for 24 hours
  5. customreaction still incomplete (1/1, ethyl acetate/heptane)
  6. customSolvents removed under reduced pressure
  7. additionWater (50 mL) and ethyl acetate (100 mL) added
  8. customThe aqueous layer is separated with ethyl acetate (3×100 mL)
  9. dry with materialdried (sodium sulfate), solids
  10. customremoved by filtration
  11. customthe solvents removed under reduced pressure
  12. customThis is purified by silica column chromatography
  13. customthe solvents are removed under reduced pressure

출처 및 근거

ORD 기록
ord-8d6df3e29a2945cf993b7050235a3b67
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383584B2

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