Cyanogen Bromide → HCID 86737777, compound

HRID 1680240Notes

Reaction equation

HRID 1680240 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 57217848HCID 57217848, compound

Product 1

HCID 86737777HCID 86737777, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4,5α-Epoxy-8β-ethyl-3-methoxy-17-methylmorphinan-6one (5.00 g, 13.7 mmole; prepared in Part A) was dissolved in 50 ml chloroform. After the addition of K2CO3 (2.84 g, 20.6 mmole), the stirred suspension was treated dropwise with a solution of cyanogen bromide (1.95 g, 18.4 mmole) in 40 ml chloroform. The mixture was stirred at room temperature for 30 minutes and heated for 1.5 hours at reflux temperature. After cooling, the insoluble material was removed from the mixture by filtration and the filtrate was evaporated to a crystalline residue which was boiled with ethanol (30 ml). After chilling, the crystals were collected to give 4.30 g (92%) of white needles, mp sinters 194° C., melts 197°-198.5° C.

Workup

  1. customprepared in Part A)
  2. temperatureheated for 1.5 hours
  3. temperatureat reflux temperature
  4. temperatureAfter cooling
  5. customthe insoluble material was removed from the mixture by filtration
  6. customthe filtrate was evaporated to a crystalline residue which
  7. temperatureAfter chilling
  8. customthe crystals were collected

Sources & evidence

ORD record
ord-30adcc00d7c94aeba6ffd24c4eb055bf
Source dataset
uspto-grants-1981_06
Patent number
US04272541

Reaction notes

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