Triethylamine → (+/-)-N-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanesulfonamide

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Reaction Steps

Triethylamine (0.014 ml) and methanesulfonyl chloride (8 μl) were added to a solution of (±)-3-[2,4-bis(methoxymethoxy)phenyl]cyclohexylamine (27 mg) in dichloromethane (1 ml), and the mixture was stirred under argon at ambient temperature. After 1 hr, the mixture was partitioned between ethyl acetate (20 ml) and sodium hydrogen carbonate (20 ml of a saturated aqueous solution). The aqueous layer was extracted with ethyl acetate (2×20 ml), and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo to furnish the title compound as an oil and a mixture of diastereoisomers; m/z (ES+) 374 (M+H)+.

Provenance & Evidence