Benzaldehyde → tert-butyl (4aS*,5R*,10bS*)-5-phenyl-3,4,4a,5,6,10b-hexahydrobenzo[h]-1,6-naphthyridine-1(2H)-carboxylate

HRID 735751노트

반응식

HRID 735751 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[N:16]1([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:21]=[CH:20][CH2:19][CH2:18][CH2:17]1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Dy+3]>C(#N)C.O>[C:2]1([C@@H:1]2[NH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C@@H:21]3[C@H:20]2[CH2:19][CH2:18][CH2:17][N:16]3[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 240BenzaldehydeHCID 6115AnilineHCID 9938788Dysprosium tris(trifluoromethanesulfonate)HCID 10465102Tert-butyl 1,2,3,4-tetrahydropyridine-1-carboxylate

생성물 1

HCID 67150720tert-butyl (4aS*,5R*,10bS*)-5-phenyl-3,4,4a,5,6,10b-hexahydrobenzo[h]-1,6-naphthyridine-1(2H)-carboxylate수율 6%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

Benzaldehyde (531 mg, 5 mmol) was dissolved in acetonitrile (15 ml), aniline (466 mg, 5 mmol) was added at 0° C., and the mixture was stirred at the same temperature for 1 hr. tert-Butyl 3,4-dihydropyridine-1(2H)-carboxylate (917 mg, 5 mmol) and Dy(OTf)3 (153 mg, 0.25 mmol) were added at 0° C., and the mixture was further stirred for 1.5 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with 6% aqueous sodium hydrogen carbonate solution and saturated brine and dried (over anhydrous MgSO4), and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using silica gel (100 g), and eluted with hexane-ethyl acetate (19:1-6:1, v/v). The title compound (4aR*,5R*,10bR*) (109 mg, 6%) was obtained as a colorless amorphous form from the first eluted fraction.

후처리

  1. stirringthe mixture was further stirred for 1.5 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with 6% aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried (over anhydrous MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. washeluted with hexane-ethyl acetate (19:1-6:1

출처 및 근거

ORD 기록
ord-9804ea1cf1d14d20a6fdaf9518affbdf
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592453B2

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