Methyl iodide → HCID 54361173, compound

HRID 1167904Notes

Reaction equation

HRID 1167904 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]([CH3:20])[CH2:5][C@@H:6]1[CH2:10][N:9]([C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:8](=[O:19])[CH2:7]1.[H-].[Na+].[CH3:23]I>CS(C)=O.O>[CH3:23][O:1][CH2:2][CH2:3][CH:4]([CH3:20])[CH2:5][C@@H:6]1[CH2:10][N:9]([C@H:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:12])[C:8](=[O:19])[CH2:7]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54144051(S)-4-(4-Hydroxy-2-methyl-butyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one

Product 1

HCID 54361173HCID 54361173, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To alcohol 89 (2 g, 7.66 mmol) in DMSO (60 mL) at room temperature was added NaH (368 mg, 60% in oil). After 30 minutes the methyl iodide (1.08 g, 7.66 mmol) was added and the solution stirred at room temperature overnight, upon which the reaction was diluted with water (500 mL). The solution was extracted with ether, and the combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography (90% to 50% hexane/acetone) of the residue gave the product 90 as an oil (1.1 g, 52%). MS m/z 290 (M+H, 100%).

Workup

  1. extractionThe solution was extracted with ether
  2. dry with materialthe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ac571303a15e49d682d0b0f2c8294d3f
Source dataset
uspto-grants-2003_09
Patent number
US06620829B2

Reaction notes

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