HCID 14698185, compound → HCID 13245269, compound

HRID 904214Notes

Reaction equation

HRID 904214 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([CH3:20])[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH:10]=[CH:11][C:12](=[O:21])[CH2:13]4>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([CH3:20])[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@H:9]3[CH2:10][CH2:11][C:12](=[O:21])[CH2:13]4

Participants

4

Reactant 1

HCID 14698185HCID 14698185, compound

Product 1

HCID 13245269HCID 13245269, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 2.0 g sample of 7,8-didehydro-3-methoxy-17-methylmorphinan-6-one (prepared as described by SAWA et al., Tetrahedron 20: 2247 [1964]) was dissolved in 300 ml of 95% ethanol and hydrogenated at 50 psi for 4 hours using 150 mg of 10% Pd/C catalyst. The solution was filtered and evaporated to yield a crystalline residue. The product was recrystallized from ethanol to give 760 mg of product, mp 187°-188.5° C. (lit. mp 188°-189° C.).

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. customto yield a crystalline residue
  4. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-874faa86a3ee4cf487d919792c638b1b
Source dataset
uspto-grants-1980_10
Patent number
US04230712

Reaction notes

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