2-Cyclopropyl-2-hydroxyacetonitrile → Naltrexone

HRID 1643351Notes

Reaction equation

HRID 1643351 reaction equation
[CH3:1][N:2]1[C@@H:12]2[CH2:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[C:16]4[O:21][C@H:6]5[C:7]([CH:9]=[CH:10][C@:11]2([OH:22])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8].[CH2:23]1[CH:25](C(O)C#N)[CH2:24]1.[H][H]>CO.[Pd].C(Cl)(Cl)Cl>[CH:19]1[C:14]2[CH2:13][C@H:12]3[N:2]([CH2:1][CH:23]4[CH2:25][CH2:24]4)[CH2:3][CH2:4][C@:5]45[C@H:6]([C:7]([CH2:9][CH2:10][C@@:11]34[OH:22])=[O:8])[O:21][C:16]([C:15]=25)=[C:17]([OH:20])[CH:18]=1

Participants

7

Reactant 3

HCID 113893592-Cyclopropyl-2-hydroxyacetonitrileHCID 1528625314-Hydroxymorphine-6-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 5360515Naltrexone

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of noroxymorphone (2 g, 6.14 mmol) in methanol (20 ml) was added cyclopropylcarboxaldehyde (0.63 ml, 8.43 mmol). 5% Palladium on carbon catalyst (1 mole % Pd) was added and the mixture was hydrogenated at 50° C. under 3 bar hydrogen pressure for 1 hour. On completion, the catalyst was filtered off and the reaction liquors diluted with chloroform (20 ml) and washed with water (3×20 ml). Evaporation of the solvent yielded naltrexone alkaloid.

Workup

  1. filtrationOn completion, the catalyst was filtered off
  2. customthe reaction liquors
  3. washwashed with water (3×20 ml)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0d3f4d3a9a6c48438f37592a57437359
Source dataset
uspto-grants-2012_02
Patent number
US08119803B2

Reaction notes

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