Methyl iodide → HCID 67777296, compound

Participants

Reaction Conditions

Reaction Steps

(3S)-3-[Benzyl-[(1S)-1-phenylethyl]amino]butan-1-ol (17.54 g, 61.9 mmol) is dissolved in anhydrous THF (186 mL) and cooled to 0° C. under an argon atmosphere. Sodium hydride (4.95 g, 60% suspension in mineral oil, 123.8 mmol) is added portionwise over 10 min. The mixture is stirred at 0° C. for 15 min, and then allowed to warm to RT. Methyl iodide (10.54 g, 74.28 mmol) is added dropwise over 30 min. After stirring for 30 additional min, the reaction is quenched by the addition of a saturated solution of NH4Cl in water. The layers are separated and the aqueous layer is extracted with diethyl ether (2×100 mL). The combined organic layers are dried over MgSO4, concentrated, and the crude is purified by normal phase chromatography (two 120 g silica-gel cartridges, 10% of methyl tert-butyl ether in hexanes) to afford the title compound as a colorless oil (14.96 g, 81%). LC-ES/MS m/z 298 (M+1).

Provenance & Evidence