Methyl iodide → HCID 86593354, compound

HRID 1071979Notes

Reaction equation

HRID 1071979 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C@@H:3]1[CH2:12][C:13]([O:15][CH3:16])=[O:14].[H-].[Na+].[CH3:19]I>CN(C=O)C.O>[CH3:19][N:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C@H:3]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[C:2]1=[O:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11172036HCID 11172036, compound

Product 1

HCID 86593354HCID 86593354, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl [(2R)-3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl]acetate (Example 1, Step 2, 650 mg, 2.95 mmol) in DMF (5 mL) at 0° C. was added NaH (142 mg, 3.54 mmol). After stirring at 0° C. for 20 minutes, MeI (220 uL, 3.54 mmol) was added and the reaction mixture was stirred for an additional 15 minutes at 0° C. The reaction mixture was then diluted with water (10 mL) and extracted with EtOAc (2×50 mL). Combined organics were washed with water (1×50 mL), dried over sodium sulfate, filtered, and concentrated to give methyl [(2R)-4-methyl-3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl]acetate, which was used without further purification. LCMS (ES) 235.1 m/z (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred for an additional 15 minutes at 0° C
  2. extractionextracted with EtOAc (2×50 mL)
  3. washCombined organics were washed with water (1×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-327bb4d8553e4ce38bb76c79a09d1b54
Source dataset
uspto-grants-2005_06
Patent number
US06908921B2

Reaction notes

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