Hydrochloric Acid → Naltrexone

HRID 627011Notes

Reaction equation

HRID 627011 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].C(=O)(O)[O-].[Na+].[I-].[Na+].[CH:30]1(CBr)[CH2:32][CH2:31]1.Cl>CN(C)C=O.C(O)C>[CH:19]1[C:14]2[CH2:13][C@H:12]3[N:2]([CH2:1][CH:30]4[CH2:32][CH2:31]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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 81503BromomethylcyclopropaneHCID 516892Sodium BicarbonateHCID 1528625314-Hydroxymorphine-6-one

Product 1

HCID 5360515Naltrexone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Steps (S1)-(S3) of Scheme 9 are as described for the corresponding reactions of Scheme 8. In step (S4) of Scheme 9, noroxymorphone prepared as described above is taken up in a solvent, e.g., ethanol or dimethyl formamide, to which sodium bicarbonate, sodium iodide, and ally bromide are added. The mixture is heated to a temperature of about 70° C. and the reaction allowed to proceed until deemed complete. The pH is adjusted with hydrochloric acid and naloxone is isolated as the hydrochloride salt. In a similar manner, in step (S5) of Scheme 9, noroxymorphone prepared as described above is taken up in a solvent, e.g., ethanol or dimethyl formamide, to which sodium bicarbonate, sodium iodide, and cyclopropylmethyl bromide are added. The mixture is heated to a temperature of about 70° C. and the reaction allowed to proceed until deemed complete. The pH is adjusted with hydrochloric acid and naltrexone is isolated as the hydrochloride salt.

Workup

  1. additionare added

Sources & evidence

ORD record
ord-bfb6550b0b06420aa05c8a457581c9be
Source dataset
uspto-grants-2016_04
Patent number
US09309258B2

Reaction notes

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