HCID 15385700, compound → HCID 15385701, compound

HRID 1858343Notes

Reaction equation

HRID 1858343 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=2)[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:32][CH2:33][O:34][CH3:35])[CH:4]=[CH:5]2>CO.[Pd]>[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH2:10][CH2:11][C@@H:12]2[O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:27]=2)[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:32][CH2:33][O:34][CH3:35])[CH:4]=[CH:5]2

Participants

4

Reactant 1

HCID 15385700HCID 15385700, compound

Product 1

HCID 15385701HCID 15385701, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4,5α-epoxy-3-methoxymethoxy-17-methyl-6α-((4-(methyloxycarbonyl)-phenyl)-methoxy)-morphinan-7-ene (1.90 g, 3.98 mmol) in MeOH (70 ml) is mixed with 10% Pd/C (1.17 g) and agitated for 0.5 hours under 1 bar of H2 pressure. The catalyst is removed by filtering through Celite and the filtrate is evaporated down. The residue is purified by flash chromatography (silica gel; mobile phase: dichloromethane: MeOH=3:1). Yield: 1.44 g 4,5α-epoxy-3-methoxymethoxy-17-methyl-6α-((4-(methyloxycarbonyl)-phenyl)-methoxy)-morphinane (75.4%).

Workup

  1. customThe catalyst is removed
  2. filtrationby filtering through Celite
  3. customthe filtrate is evaporated down
  4. customThe residue is purified by flash chromatography (silica gel; mobile phase: dichloromethane: MeOH=3:1)

Sources & evidence

ORD record
ord-df1538998ace409f91357ff0469c86da
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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