Methyl iodide → (R)-4-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-3,4-dimethyl-oxazolidin-2-one

HRID 2389096Notes

Reaction equation

HRID 2389096 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25][C:24](=[O:27])[NH:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:31]I>C1COCC1.CN(C=O)C>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C@:22]2([CH3:28])[CH2:26][O:25][C:24](=[O:27])[N:23]2[CH3:31])[CH:16]=[CH:15]3)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 67414115(R)-4-[6-(4-tert-Butylcyclohexyloxy)naphthalen-2-yl]-4-methyl-oxazolidin-2-one

Product 1

HCID 67414727(R)-4-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-3,4-dimethyl-oxazolidin-2-oneYield 106.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-4-[6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (73 mg, 0.19 mmol) in THF (1 mL) and DMF (1 mL) was added sodium hydride (60% in mineral oil, 12 mg, 0.29 mmol). After the mixture was stirred at room temperature for 2 hrs, methyl iodide (60 μL, 0.96 mmol) was added. The mixture was stirred at room temperature for 3 hrs. LCMS showed about 30% of conversion. Additional sodium hydride (60% in mineral oil, 50 mg) was added. After the mixture was stirred at room temperature overnight, the mixture was partitioned between NH4Cl aq and EtOAc. The organic phase was washed with water, dried over anhydrous MgSO4, filtered, and concentrated to give 80 mg of crude product, 106%. ESI-MS (M+H)+: 396.20, room temperature 2.53 min.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hrs
  2. stirringAfter the mixture was stirred at room temperature overnight
  3. customthe mixture was partitioned between NH4Cl aq and EtOAc
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-132527cb149f40c9901a211700466a5b
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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