Cyanogen Bromide → HCID 86737778, compound

HRID 1680244Notes

Reaction equation

HRID 1680244 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[C@H:10]([CH2:21][CH3:22])[CH2:11][C:12]2=[O:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:23][CH3:24])[CH:4]=[CH:5]2.C([O-])([O-])=O.[K+].[K+].[N:31]#CBr>C(Cl)(Cl)Cl>[C:19]([N:18]1[CH2:17][CH2:16][C@:14]23[C:15]4[C:2]5[O:1][C@H:13]2[C:12](=[O:20])[CH2:11][C@@H:10]([CH2:21][CH3:22])[C@H:9]3[C@H:8]1[CH2:7][C:6]=4[CH:5]=[CH:4][C:3]=5[O:23][CH3:24])#[N:31]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 70572918HCID 70572918, compound

Product 1

HCID 86737778HCID 86737778, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4,5α-Epoxy-8α-ethyl-3-methoxy-17-methylmorphinan-6-one 3 (6.50 g, 19.8 mmole) was dissolved in chloroform (100 ml). After the addition of K2CO3 (4.12 g, 29.8 mmole), the stirred suspension was treated dropwise with a solution of cyanogen bromide (2.50 g, 23.8 mmole) in 50 ml of chloroform. After the addition was complete, the mixture was heated to reflux and refluxed for 2 hours. Cooling was followed by removal of the insoluble material by filtration. The filtrate was evaporated to a residue which crystallized on coevaporation with ethanol. The crystals were suspended in hot ethanol, the mixture cooled and the crystals collected to give 6.30 g (94%) of 5 as white needles, mp 212°-217°, in two crops.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux
  4. temperaturerefluxed for 2 hours
  5. temperatureCooling
  6. customwas followed by removal of the insoluble material by filtration
  7. customThe filtrate was evaporated to a residue which
  8. customcrystallized on coevaporation with ethanol
  9. temperaturethe mixture cooled
  10. customthe crystals collected

Sources & evidence

ORD record
ord-5290463303574ab69732fa395767f3e8
Source dataset
uspto-grants-1981_06
Patent number
US04272541

Reaction notes

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