Hydrochloric Acid → HCID 57217848, compound

HRID 1680239Notes

Reaction equation

HRID 1680239 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[C@@H:10]([CH:21]=[CH2:22])[CH2:11][C:12]2=[O:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:23][CH3:24])[CH:4]=[CH:5]2.Cl>C(O)C.[Pd]>[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[C@@H:10]([CH2:21][CH3:22])[CH2:11][C:12]2=[O:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:23][CH3:24])[CH:4]=[CH:5]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70574375HCID 70574375, compound

Product 1

HCID 57217848HCID 57217848, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4,5α-epoxy-3-methoxy-17-methyl-8β-vinylmorphinan-6-one (9.0 g) in 95% ethanol was added 2 ml of concentrated hydrochloric acid followed by 10% palladium/charcoal (1.0 g.). The mixture was hydrogenated at an initial pressure of 50 psi for 2.5 hours. The reaction mixture was filtered, the filtrate made acidic by the addition of hydrochloric acid and evaporated to a crystalline solid. The solid was recrystallized from ethyl acetate with the addition of ethanol to give, after drying, 8.7 g (90%) of the 8-ethyl product TR-5059.HCl, mp 285°-288° C.

Workup

  1. customfor 2.5 hours
  2. filtrationThe reaction mixture was filtered
  3. additionthe filtrate made acidic by the addition of hydrochloric acid
  4. customevaporated to a crystalline solid
  5. customThe solid was recrystallized from ethyl acetate with the addition of ethanol
  6. customto give
  7. customafter drying

Sources & evidence

ORD record
ord-00e03bc1a5834d2591d5fd8cd074b0d8
Source dataset
uspto-grants-1981_06
Patent number
US04272541

Reaction notes

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