Ethanol → HCID 13145942, compound

HRID 2166943Notes

Reaction equation

HRID 2166943 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C@:15]34[CH2:17][CH2:18][N:19](C(OCC(Cl)(Cl)Cl)=O)[C@@H:9]([C@:10]3(C(OCC(Cl)(Cl)Cl)=O)[CH2:11][CH2:12][C:13](=[O:28])[CH2:14]4)[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[NH4+].[Cl-].C([OH:41])C>[Zn]>[OH:41][C@:10]12[C@@H:9]3[NH:19][CH2:18][CH2:17][C@:15]1([C:16]1[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=1[CH2:8]3)[CH2:14][C:13](=[O:28])[CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 56999615HCID 56999615, compound

Product 1

HCID 13145942HCID 13145942, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

To a mixture of 2.9 g (4.54 mmol) 4-methoxy-N,14-bis(2,2,2-trichloroethoxycarbonyl)-morphinan-6-one in 130 ml ethanol were added 15 g (280.4 mmol) NH4Cl and this mixture was stirred and refluxed. During 0.5 h 12 g (177 mg) activated zinc powder were added portionwise and the resulting mixture was refluxed for 1 h. After cooling and filtration, the filtrate was evaporated. The residue was dissolved in water, basified with saturated NaHCO3 solution and extracted with CHCl3. The organic layer was washed with brine, dried and evaporated to give an oil which was crystallized with isopropyl ether to yield 690 mg (53%) 14-hydroxy-4-methoxymorphinan-6-one, m.p. 137°-139°, [α]D26 --66.5°. (C 1.08, CHCl3).

Workup

  1. temperaturerefluxed
  2. temperaturethe resulting mixture was refluxed for 1 h
  3. temperatureAfter cooling
  4. filtrationfiltration
  5. customthe filtrate was evaporated
  6. dissolutionThe residue was dissolved in water
  7. extractionextracted with CHCl3
  8. washThe organic layer was washed with brine
  9. customdried
  10. customevaporated
  11. customto give an oil which
  12. customwas crystallized with isopropyl ether

Sources & evidence

ORD record
ord-d9636d4f5cee4b6e9ca1712c76f986f7
Source dataset
uspto-grants-1983_06
Patent number
US04390699

Reaction notes

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