Acetone → Methylnaltrexone Bromide

HRID 47066

Reaction equation

HRID 47066 reaction equation
[CH2:1]1[CH:3]([CH2:4][N:5]2[C@@H:15]3[CH2:16][C:17]4[CH:22]=[CH:21][C:20]([OH:23])=[C:19]5[O:24][C@H:9]6[C:10]([CH2:12][CH2:13][C@:14]3([OH:25])[C@:8]6([C:18]=45)[CH2:7][CH2:6]2)=[O:11])[CH2:2]1.[CH3:26]C(C)=O.C[Br:31]>CN(C)C=O>[CH3:26][N+:5]1([CH2:4][CH:3]2[CH2:2][CH2:1]2)[C@@H:15]2[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[C:19]4[O:24][C@H:9]5[C:10]([CH2:12][CH2:13][C@:14]2([OH:25])[C@:8]5([C:18]=34)[CH2:7][CH2:6]1)=[O:11].[Br-:31]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6323Methyl BromideHCID 5360515Naltrexone

Product 1

HCID 5361917Methylnaltrexone Bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 gm (7.35 millimols) of N-cyclopropylmethylnoroxymorphone were dissolved in a mixture consisting of 50 ml of absolute acetone and 0.5 ml of dimethylformamide, and the resulting solution was admixed with 4.25 gm (44.8 millimols) of methyl bromide. The reaction mixture was then allowed to stand for three weeks at room temperature in a sealed pressure vessel. Thereafter, the contents of the vessel were evaporated, and the residue was crystallized from methanol and recrystallized from methanol/ether, yielding 1.0 gm of the methobromide which had a melting point of 253° C.

Workup

  1. waitto stand for three weeks at room temperature in a sealed pressure vessel
  2. customThereafter, the contents of the vessel were evaporated
  3. customthe residue was crystallized from methanol
  4. customrecrystallized from methanol/ether
  5. customyielding 1.0 gm of the methobromide which

Sources & evidence

ORD record
ord-8fd4968a3ead4b3c877730306a53b82c
Source dataset
uspto-grants-1979_11
Patent number
US04176186

Linked notes

Loading…