Methyl iodide → HCID 54361173, compound

Participants

Role	Name	HCID	Charge
Reactant	Methyl iodide	HCID 6328	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	(S)-4-(4-Hydroxy-2-methyl-butyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one	HCID 54144051	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Water	HCID 962	—
Product	HCID 54361173	HCID 54361173	52%

Reaction Steps

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%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07189747B2
Source dataset	uspto-grants-2007_03
ORD ID	ord-fc565534547c48adbfa9109b0ccb4fe7
Source note	uspto-grants-2007_03