HCID 57018033, compound → HCID 57302556, compound

HRID 544556Notes

Reaction equation

HRID 544556 reaction equation
[CH:1]1([CH2:5][N:6]2[CH2:24][CH2:23][C@:13]34[C:14]5[C:15]6[O:22][CH:12]3[C:11](=[O:25])[CH2:10][CH2:9][C@@:8]4([F:26])[C@H:7]2[CH2:20][C:19]=5[CH:18]=[CH:17][C:16]=6[OH:21])[CH2:4][CH2:3][CH2:2]1>O1CCCC1>[CH:1]1([CH2:5][N:6]2[CH2:24][CH2:23][C@:13]34[C:14]5[C:15]6[O:22][CH:12]3[CH:11]([OH:25])[CH2:10][CH2:9][C@@:8]4([F:26])[C@H:7]2[CH2:20][C:19]=5[CH:18]=[CH:17][C:16]=6[OH:21])[CH2:2][CH2:3][CH2:4]1

Participants

3

Reactant 1

HCID 57018033HCID 57018033, compound

Product 1

HCID 57302556HCID 57302556, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17-(Cyclobutylmethyl)-4,5-epoxy-14-fluoro-3-hydroxymorphinan-6-one (1.1 g) was dissolved in tetrahydrofuran (50 ml) and dried over molecular sieves. This dried solution was then added to a solution of lithium tri(tertiarybutoxy)aluminum hydride (7.5 g in 50 ml THF) and stirred for three hours. Excess reducing agent was decomposed by cautious addition of water followed by sodium carbonate to pH 8.2. The aqueous tetrahydrofuran was filtered off, and the filter cake washed with tetrahydrofuran to leach out the adhering product. The organic solvent was removed by evaporation, the residue dissolved in chloroform, and the chloroform solution washed with water and filtered through a fluted filter. Evaporation of the chloroform yielded 800 mg of a solid which was recrystallized from ethanol to give the title product, m.p. 236°-239°.

Workup

  1. customdried over molecular sieves
  2. additionThis dried solution was then added to a solution of lithium tri(tertiarybutoxy)aluminum hydride (7.5 g in 50 ml THF)
  3. additionwas decomposed by cautious addition of water
  4. filtrationThe aqueous tetrahydrofuran was filtered off
  5. washthe filter cake washed with tetrahydrofuran
  6. customThe organic solvent was removed by evaporation
  7. dissolutionthe residue dissolved in chloroform
  8. washthe chloroform solution washed with water
  9. filtrationfiltered through
  10. filtrationa fluted filter
  11. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-da4aa92f9040449e98843f1cc42e5b3e
Source dataset
uspto-grants-1984_05
Patent number
US04451470

Reaction notes

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