N,N'-Dimethylethylenediamine → HCID 89814001, compound

HRID 525407Notes

Reaction equation

HRID 525407 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.Br[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:26])[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])=[C:18]([CH3:26])[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 2733820(S)-(+)-5,5-Dimethyl-4-phenyl-2-oxazolidinoneHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 89814001HCID 89814001, compoundYield 90%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
140 °C

Procedure

A microwave vial was charged with (S)-5,5-dimethyl-4-phenyloxazolidin-2-one (commercially available from Sigma-Aldrich, Milwaukee, Wis., 0.100 g, 0.523 mmol), methyl 4-bromo-2-methylbenzoate (commercially available from Sigma-Aldrich, Milwaukee, Wis., 0.132 g, 0.575 mmol), tribasic potassium phosphate (0.555 g, 2.61 mmol) and dioxane (3.50 mL). The mixture was purged with argon and then copper (I) iodide (0.100 g, 0.523 mmol) and N,N′-dimethylethylenediamine (0.113 mL, 1.046 mmol) were added. The system was purged with argon, the tube was sealed, and the reaction mixture was heated at 140° C. for 1 hour in a microwave. The reaction mixture was filtered through Celite® brand filter aid and the filtrate was concentrated to afford an orange brown solid. The solid thus obtained was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-50% EtOAc-hexane) to afford (S)-methyl 4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-2-methylbenzoate (0.159 g, 0.468 mmol, 90% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.90 (s, 3H), 1.63 (s, 3H), 2.43 (s, 3H), 3.75 (s, 3H), 5.52 (s, 1H), 7.03-7.46 (m, 6H), 7.50 (d, J=2.35 Hz, 1H), 7.75 (d, J=8.71 Hz, 1H). m/z (ESI) 340 (M+H)+.

Workup

  1. customThe mixture was purged with argon
  2. customThe system was purged with argon
  3. customthe tube was sealed
  4. filtrationThe reaction mixture was filtered through Celite® brand
  5. filtrationfilter aid
  6. concentrationthe filtrate was concentrated
  7. customto afford an orange brown solid
  8. customThe solid thus obtained
  9. customwas purified

Sources & evidence

ORD record
ord-fb2bfbfc0c0a4b6883992f971a35d24e
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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