Ammonium Hydroxide → HCID 57202909, compound

HRID 544553Notes

Reaction equation

HRID 544553 reaction equation
B(Br)(Br)Br.[CH:5]1([CH2:8][N:9]2[CH2:28][CH2:27][C@:16]34[C:17]5[C:18]6[O:26][CH:15]3[C:14](=[O:29])[CH2:13][CH2:12][C@@:11]4([F:30])[C@H:10]2[CH2:23][C:22]=5[CH:21]=[CH:20][C:19]=6[O:24]C)[CH2:7][CH2:6]1.[OH-].[NH4+]>C(Cl)(Cl)Cl>[CH:5]1([CH2:8][N:9]2[CH2:28][CH2:27][C@:16]34[C:17]5[C:18]6[O:26][CH:15]3[C:14](=[O:29])[CH2:13][CH2:12][C@@:11]4([F:30])[C@H:10]2[CH2:23][C:22]=5[CH:21]=[CH:20][C:19]=6[OH:24])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 57148950HCID 57148950, compound

Product 1

HCID 57202909HCID 57202909, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Boron tribromide (2.5 ml) was dissolved in chloroform (75 ml), and chilled to 20°-25°. A solution of 17-(cyclopropylmethyl)-4,5-epoxy-14-fluoro-3-methoxymorphinan-6-one (1.25 g in 25 ml chloroform) was added and the mixture stirred at that temperature for one-half hour. The reaction mixture was then dumped with good stirring onto 80 g of ice containing 5 ml of concentrated ammonium hydroxide at approximately pH 9.2. The chloroform solution was vigorously shaken, washed with water, then extracted with 5% sodium hydroxide solution. The alkali extract was then separated, acidified, and the liberated phenolic compound taken up in chloroform, washed, and dried over molecular sieve. The dried solvent extract was evaporated, and the crude product column chromatographed using silica gel and, as eluant, a solvent mixture comprising 95% chloroform and 5% ethanol. The purified product was crystallized from ethanol, m.p. 188°-190°.

Workup

  1. temperaturechilled to 20°-25°
  2. washwashed with water
  3. extractionextracted with 5% sodium hydroxide solution
  4. extractionThe alkali extract
  5. customwas then separated
  6. washwashed
  7. customdried over molecular sieve
  8. extractionThe dried solvent extract
  9. customwas evaporated
  10. customthe crude product column chromatographed
  11. customThe purified product was crystallized from ethanol, m.p. 188°-190°

Sources & evidence

ORD record
ord-247df042815a4525ac548fcdcaf3d943
Source dataset
uspto-grants-1984_05
Patent number
US04451470

Reaction notes

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