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

HRID 550286Notes

Reaction equation

HRID 550286 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e938a3c24bca4f1b948635c30e3c9602
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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