Triethylamine → Naloxone

HRID 2275308Notes

Reaction equation

HRID 2275308 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:23](OCC=C)(=O)[CH3:24].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:23]=[CH:24][CH2:1][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]([CH2:9][CH2:10][C@:11]2([OH:22])[C@:5]5([C:15]=34)[CH2:4][CH2:3]1)=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11584Allyl acetateHCID 1528625314-Hydroxymorphine-6-one2×

Product 1

HCID 5284596Naloxone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

In one embodiment, allylation of noroxymorphone with allyl acetate is accomplished by combining noroxymorphone with triethylamine (3 equivalents), toluene (50 mL) and tetrakis(triphenylphosphine)palladium[0] (0.1 equivalent), and heating the mixture at 80° C. for 64 hours. The mixture is cooled to a temperature of about 20° C. and filtered through a plug of CELITE and the filtrate was concentrated under reduced pressure. Naloxone is isolated from the concentrated filtrate using normal extractive procedures.

Workup

  1. temperatureThe mixture is cooled to a temperature of about 20° C.
  2. filtrationfiltered through a plug of CELITE
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e4aeda43d8349729d5f4759541f7733
Source dataset
uspto-grants-2015_09
Patent number
US09127014B2

Reaction notes

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