Triethylamine → 3-[(S)-1-(4-bromophenyl)ethyl]-6-isopropyl-6-(2-methylallyl)-1,3-oxazinan-2-one

Participants

Reaction Steps

To a solution of 3-{(S)-2-[1-(4-bromophenyl)-ethylamino]-ethyl}-2,5-dimethyl-hex-5-en-3-ol (6.4 g, 16.8 mmol) and triethylamine (5.34 g, 52 mmol) in CH2Cl2 (260 mL) was added triphosgene (2.52 g, 8.5 mmol) at 0° C. under N2, and the mixture was stirred at room temperature overnight. The reaction was quenched with water, and the mixture was extracted with CH2Cl2 (3×50 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by column chromatography to give two isomers of 3-[(S)-1-(4-bromophenyl)ethyl]-6-isopropyl-6-(2-methylallyl)-1,3-oxazinan-2-one.

Provenance & Evidence