Acetic Acid → 11-Diethylaminocarbonyl-10-methyl-7-(2-propenyl)-5,6,7,8,12,12b-hexahydro-4,8-methanobenzofuro[3,2-e]pyrrolo[2,3-g]isoquinoline-1,8a-(9H)-diol hydrochloride

HRID 1602215Notes

Reaction equation

HRID 1602215 reaction equation
[CH2:1]=[CH:2][CH2:3][N:4]1[C@@H:21]2[CH2:22][C:9]3C=CC(O)=C4O[C@H:15]5[C:16]([CH2:18][CH2:19][C@:20]2([OH:23])[C@:7]5([C:8]=34)[CH2:6][CH2:5]1)=O.[ClH:25].[CH2:26]([N:28]([CH2:43][CH3:44])[C:29](=[O:42])[C:30](=[N:34]NC1C=CC=CC=1)[C:31](=O)[CH3:32])[CH3:27].[CH3:45][C:46]([O:48][Na])=O.[C:50]([OH:53])(=O)[CH3:51]>[Zn]>[ClH:25].[CH2:43]([N:28]([CH2:26][CH3:27])[C:29]([C:30]1[NH:34][C:16]2[CH:15]3[O:48][C:46]4=[C:45]5[C:7]63[C:20]([OH:23])([CH2:19][C:18]=2[C:31]=1[CH3:32])[CH:21]([CH2:22][C:9]5=[CH:8][CH:51]=[C:50]4[OH:53])[N:4]([CH2:3][CH:2]=[CH2:1])[CH2:5][CH2:6]6)=[O:42])[CH3:44]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5464092Naloxone HydrochlorideHCID 178418240HCID 178418240, compoundHCID 178418247HCID 178418247, compound

Product 1

HCID 8675477011-Diethylaminocarbonyl-10-methyl-7-(2-propenyl)-5,6,7,8,12,12b-hexahydro-4,8-methanobenzofuro[3,2-e]pyrrolo[2,3-g]isoquinoline-1,8a-(9H)-diol hydrochloride

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

1.0 g (2.75 mmoles) of naloxone hydrochloride, 2.15 g (8.25 mmoles) di N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.68 g (8.25 mmoles) of CH3COONa, 1.06 g (16.2 mmoles) of zinc dust and 15 ml of glacial acetic acid were treated as described in the Example 1. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 80:20:0.5), dissolved in MeOH and the solution brought to acidic pH with HCl/Et2O. The precipitate was filtered and recrystallized twice from EtOH to yield 0.95 g of the title compound.

Workup

  1. customThe residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 80:20:0.5)
  2. dissolutiondissolved in MeOH
  3. filtrationThe precipitate was filtered
  4. customrecrystallized twice from EtOH

Sources & evidence

ORD record
ord-fd0f937d339041e088b45b75b4293114
Source dataset
uspto-grants-1999_11
Patent number
US05981540

Reaction notes

Loading…