Methyl iodide → HCID 54361173, compound

HRID 479034Notes

Reaction equation

HRID 479034 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-1a7cc63e725c4f439df9b155f637fb0f
Source dataset
uspto-grants-2003_11
Patent number
US06642398B2

Reaction notes

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