Ammonium Chloride → HCID 19776678, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the N-benzyl morpholin-3-one (4.46 g, 23.4 mmol) obtained in (i) in tetrahydrofuran (25 ml) was added dropwise over a period of 15 minutes to a solution of lithium diisopropylamide (28.0 mmol [prepared from diisopropylamine (3.93 ml, 28.0 mmol) and n-butyl lithium (2.5 M in hexanes, 11.2 ml, 28.0 mmol)]) in tetrahydrofuran (50 ml), with stirring, at -78° C. The resulting solution was stirred for 45 minutes and then 4-tert-butylbenzyl bromide (6.0 ml, 32.7 mmol) in tetrahydrofuran (25 ml) was added dropwise over a period of 10 minutes. The reaction mixture was stirred for 90 minutes and then warmed to room temperature. Addition of water (25 ml) and saturated aqueous ammonium chloride (25 ml) was followed by extraction of the aqueous phase by ethyl acetate (3×20 ml). The combined organic phases were washed with brine (20 ml), dried with sodium sulphate and evaporated in vacuo. Flash column chromatography of the resulting oil upon silica gel using hexane: ethyl acetate (1:1) as eluant afforded the desired product as a clear, faintly yellow oil, 5.29 g, M+ found: 337.

Provenance & Evidence