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

HRID 735751ノート

反応式

HRID 735751 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9804ea1cf1d14d20a6fdaf9518affbdf
出典データセット
uspto-grants-2009_09
特許番号
US07592453B2

反応ノート

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