N,N'-Dimethylethylenediamine → (S)-methyl 4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoate

HRID 525318Notes

Reaction equation

HRID 525318 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C:5](=[O:7])[NH:4][C@H:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.I[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O1CCOCC1>[CH3:1][C:2]1([CH3:14])[O:6][C:5](=[O:7])[N:4]([C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[C@H:3]1[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 69273Methyl 4-iodobenzoateHCID 2733820(S)-(+)-5,5-Dimethyl-4-phenyl-2-oxazolidinone

Product 1

HCID 71680861(S)-methyl 4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoateYield 93%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a round bottom flask were added (S)-5,5-dimethyl-4-phenyloxazolidin-2-one (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (1.717 g, 8.98 mmol), methyl 4-iodobenzoate (commercially available from Sigma-Aldrich, Milwaukee, Wis.) (2.353 g, 8.98 mmol), and dioxane (90 mL). Tribasic potassium phosphate (9.53 g, 44.9 mmol), and copper (I) iodide (1.710 g, 8.98 mmol) were then added to the flask. The vessel was purged with nitrogen and N,N′-dimethylethylenediamine (1.933 mL, 17.96 mmol) was added. The suspension was heated at reflux overnight yielding a tan suspension. The mixture was filtered through Celite® brand filter aid, and the filtrate was dried under reduced pressure providing (S)-methyl 4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)benzoate (2.72 g, 8.36 mmol, 93% yield) as a light green oil which was used in the next step. 1H NMR (400 MHz, CDCl3) δ=7.94-7.90 (m, 2H), 7.55-7.51 (m, 2H), 7.39-7.32 (m, 3H), 7.21-7.16 (m, 2H), 5.04 (s, 1H), 3.86 (s, 3H), 1.70 (s, 3H), 1.02 (s, 3H).

Workup

  1. additionwas added
  2. temperatureThe suspension was heated
  3. temperatureat reflux overnight
  4. customyielding a tan suspension
  5. filtrationThe mixture was filtered through Celite® brand
  6. filtrationfilter aid
  7. customthe filtrate was dried under reduced pressure

Sources & evidence

ORD record
ord-d53dc417ddf3408e9a92eefb1119a25a
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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