Methyl iodide → (R)-4-benzyl-3-((R)-2-(4-bromophenyl)propanoyl)oxazolidin-2-one

HRID 735696Notes

Reaction equation

HRID 735696 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][Si]([N-][Si](C)(C)C)(C)C.[Na+].CI>C1COCC1>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:23])[C@@H:15]([C:16]1[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][CH:21]=1)[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 54374212HCID 54374212, compound

Product 1

HCID 54029560(R)-4-benzyl-3-((R)-2-(4-bromophenyl)propanoyl)oxazolidin-2-oneYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 76A (380 mg, 1.01 mmol) in THF (5 mL) at −78° C., was added NaHMDS (1.3 mL, 1.0M, 1.3 mmol), dropwise. The solution was stirred at −78° C. for 3 h. A solution of MeI (0.62 mL, 10 mmol) in 2 mL THF was added. The solution was stirred −78° C. for 3 h, and −40° C. for 1 h. The reaction was quenched with sat. NH4Cl and extracted with EtOAc (3×20 mL). The organic layer washed with brine, dried (Na2SO4), and concentrated. Purification via flash chromatography (0-30% EtOAc in hexanes) gives 76B (70 mg, 18%). MS (ESI) m/z 388.3 (M+H)+.

Workup

  1. stirringThe solution was stirred −78° C. for 3 h
  2. wait−40° C. for 1 h
  3. customThe reaction was quenched with sat. NH4Cl
  4. extractionextracted with EtOAc (3×20 mL)
  5. washThe organic layer washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification via flash chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-65bfaf85709f4008ac9e8bd568a00f96
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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