Water → HCID 70152942, compound

HRID 1017250Notes

Reaction equation

HRID 1017250 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19](I)=[CH:18][C:17]=2[O:23][CH3:24])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O:26][C:27]([Sn](C)(C)C)=[CH2:28].[OH2:33]>C1COCC1>[C:17]([OH:23])(=[O:26])[C:16]([OH:15])=[O:33].[C:27]([C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH:10]2[O:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9]2)=[C:17]([O:23][CH3:24])[CH:18]=1)(=[O:26])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 11328099HCID 11328099, compoundHCID 12824445HCID 12824445, compound

Product 1

HCID 70152942HCID 70152942, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(±)-4-Benzyl-2-[(4-iodo-2-methoxyphenoxy)methyl]morpholine (360 mg, 0.82 mmol), 1-methoxyvin-1-yl trimethyltin (528 mg, 2.4 mmol), and palladium bis(triphenylphosphine)palladium(II)chloride (36 mg, 0.052 mmol) were refluxed in THF (15 ml) for 24 h. Water was added and was followed by extraction twice with ethyl acetate. The solvent was evaporated and the residue was stirred in aqueous hydrochloric acid (25 ml, 1 M) and methanol (10 ml) at 50° C. for 1 h. The product was extracted with ethyl acetate. Drying and evaporation of the solvent was followed by chromatography. The product was dissolved in ether and precipitated as the oxalate. Yield 40 mg. mp 122-127° C.

Workup

  1. extractionwas followed by extraction twice with ethyl acetate
  2. customThe solvent was evaporated
  3. extractionThe product was extracted with ethyl acetate
  4. customDrying
  5. customevaporation of the solvent
  6. dissolutionThe product was dissolved in ether
  7. customprecipitated as the oxalate

Sources & evidence

ORD record
ord-e1d3bace9d044757afbb0cba7f70e7c3
Source dataset
uspto-grants-2002_11
Patent number
US06479491B1

Reaction notes

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