Cyanogen Bromide → HCID 86737787, compound

HRID 1680229Notes

Reaction equation

HRID 1680229 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:19]([CH3:20])[CH2:18][CH2:17][C@@:14]4([C:15]=2[CH:16]=1)[C@@:9]3([O:23][CH3:24])[C@H:10]([CH3:22])[CH2:11][C:12](=[O:21])[CH2:13]4.C(=O)([O-])[O-].[K+].[K+].[N:31]#CBr>C(Cl)Cl>[C:20]([N:19]1[CH2:18][CH2:17][C@@:14]23[C:15]4[CH:16]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=4[CH2:7][C@@H:8]1[C@:9]2([O:23][CH3:24])[C@H:10]([CH3:22])[CH2:11][C:12](=[O:21])[CH2:13]3)#[N:31]

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 70567637HCID 70567637, compound

Product 1

HCID 86737787HCID 86737787, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,14-dimethoxy-8α,17-dimethylmorphinan-6-one (24) (0.1 g, 0.303 mmol) in methylene chloride (3 ml) was added anhydrous potassium carbonate (0.23 g) followed by cyanogen bromide (0.2 g). The mixture was refluxed overnight under a nitrogen atmosphere with stirring. After cooling, the solution was filtered and the residue washed with excess methylene chloride. The filtrate was concentrated under reduced pressure to give 0.103 g (99% theory) of 17-cyano-3,14-dimethoxy-8α-methylmorphinan-6-one (25) as a foamy solid. Examination by thin layer chromatography showed a single spot (silica gel plates; solvent system CHCl3 :MeOH, 90:10). The product was used in the next reaction without purification.

Workup

  1. temperatureThe mixture was refluxed overnight under a nitrogen atmosphere
  2. temperatureAfter cooling
  3. filtrationthe solution was filtered
  4. washthe residue washed with excess methylene chloride
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f091608f40324699a7e60f5bfd41c832
Source dataset
uspto-grants-1981_06
Patent number
US04272540

Reaction notes

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