Water → HCID 57017342, compound

HRID 1680217Notes

Reaction equation

HRID 1680217 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@@:9]3([O:22][CH3:23])[CH:10]=[CH:11][C:12](=[O:21])[CH2:13]4.[H][H].O.C(=O)(O)[O-].[K+]>C(O)(=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@@:9]3([O:22][CH3:23])[CH2:10][CH2:11][C:12](=[O:21])[CH2:13]4

Participants

7

Reactant 4

HCID 962WaterHCID 516893Potassium BicarbonateHCID 57085542HCID 57085542, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57017342HCID 57017342, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 7,8-didehydro-3,14-dimethoxy-17-methylmorphinan-6-one (3) (4.30 g, 13.72 mmol) in acetic acid (80 ml) was hydrogenated over 1.72 g of Pd/C (10%) at 3 atmospheres pressure until the hydrogen uptake was complete. The mixture was filtered through Celite and the solution concentrated under reduced pressure to give a clear oil. This oil was treated with water (100 ml) and potassium bicarbonate was added until the solution became basic. The mixture was extracted with methylene chloride (3×100 ml) whereupon the organic layer was separated, dried over MgSO4 and filtered. The filtrate was concentrated under vacuum to give 4.19 g (97% theory) of the desired product as a colorless solid (m.p. 152°-156° C.).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe solution concentrated under reduced pressure
  3. customto give a clear oil
  4. additionwas added until the solution
  5. extractionThe mixture was extracted with methylene chloride (3×100 ml) whereupon the organic layer
  6. customwas separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-39eb7efeb43a484185c9e66ef96fc14a
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

Loading…