Triphenylphosphine → HCID 54348392, compound

HRID 840101Notes

Reaction equation

HRID 840101 reaction equation
[O:1]1[CH: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:12]2=[O:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3](OS(C(F)(F)F)(=O)=O)[CH:4]=[CH:5]2.[CH2:29]([O:31][C:32]([Sn](CCCC)(CCCC)CCCC)=[CH2:33])[CH3:30].[Li+].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH4+:18].[OH-:1].[O:1]1[CH: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:12]2=[O:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([C:29]([O:31][CH2:32][CH3:33])=[CH2:30])[CH:4]=[CH:5]2

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 54452086HCID 54452086, compound

Product 2

HCID 14923Ammonium HydroxideHCID 54348392HCID 54348392, compoundYield 191.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

2.5 g (6.0 mmol) of 4,5-epoxy-17-methyl-3-trifluoromethanesulfonyloxymorphinan-6-one, 2.1 ml (6.2 mmol) of (1-ethoxyvinyl)tributyltin, 2 g (48 mmol) of LiCl, 0.42 g (0.6 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.63 g (2.4 mmol) of triphenylphosphine in 25 ml of dimethylformamide were treated as described in Preparation 2. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2/MeOH/conc. NH4OH 90:7:0.7 respectively, yielding 1.95 g of the title product.

Workup

  1. customas described in Preparation 2
  2. customThe crude reaction mixture
  3. customwas purified by flash chromatography
  4. washeluting with a mixture CH2Cl2/MeOH/conc

Sources & evidence

ORD record
ord-54655f0de3c94a8c8ce6062da9ff2730
Source dataset
uspto-grants-2002_04
Patent number
US06365594B1

Reaction notes

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