Acetic Acid → (+)(4aR,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-Decahydro-6-((4-methoxyphenyl)methyl)quinoline

HRID 399541Notes

Reaction equation

HRID 399541 reaction equation
COC1C=CC(C[CH:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]2C(C2C=CC=CC=2)C)=CC=1.[C:28](O)(=[O:30])C.Cl.[CH3:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].[CH3:39]O>C(OCC)C.[Pd]>[CH3:28][O:30][C:35]1[CH:34]=[CH:33][C:38]([CH2:39][C@@H:15]2[CH2:14][CH2:13][C@H:12]3[C@H:17]([CH2:18][CH2:19][CH2:10][NH:11]3)[CH2:16]2)=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 21896459Hexane methanolHCID 131720884(4-Methoxyphenyl)methyl-1-(1'-phenylethyl)quinoline

Product 1

HCID 18665874(+)(4aR,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-Decahydro-6-((4-methoxyphenyl)methyl)quinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

(-)-(1'S,4aS,6R,8aS)-1,2,3,4,4a,5,6,7,8,8a-Decahydro-6-((4-methoxyphenyl)methyl-1-(1'-phenylethyl)quinoline (1.32 g, prepared according to Example 14) in n-hexane:MeOH (1:1, 80 ml) with 10% Pd/C (0.2 g) and glacial acetic acid (5 ml) was hydrogenated at 50 psi for 15 hours. The solution was filtered, evaporated under reduced pressure and the residue treated with sodium carbonate solution to give a product which was extracted into ethyl acetate. The ethyl acetate extract was dried (MgSO4) and evaporated to give a gum. This was dissolved in diethyl ether and treated with ethereal HCl. The resulting precipitate was collected by filtration and dried giving the title compound as the hydrochloride salt (0.7 g), mp 226°-8° C. [α]26D =+38° (1% in MeOH).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated under reduced pressure
  3. additionthe residue treated with sodium carbonate solution
  4. customto give a product which
  5. extractionwas extracted into ethyl acetate
  6. extractionThe ethyl acetate extract
  7. dry with materialwas dried (MgSO4)
  8. customevaporated
  9. customto give a gum
  10. filtrationThe resulting precipitate was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-d9f50c1de3694902a2279278999a17d2
Source dataset
uspto-grants-1998_10
Patent number
US05821251

Reaction notes

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