Triethylamine → HCID 66870053, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2-(4-bromophenyl)propan-2-ylamino)-5-methyl-3-phenylhex-5-en-3-ol (60 mg, 149.3 μmol) in CH2Cl2 (15 mL) was added Et3N (75.5 mg, 746.3 μmol). The mixture was cooled to 0° C. and triphosgene (44.3 mg, 149.3 μmol) was added under nitrogen. The solution was stirred at 0° C. for 1 h. The reaction was quenched with water (15 mL) and extracted with CH2Cl2 (15 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrate under vacuum. The residue was purified by preparative TLC (petroleum ether: EtOAc =3:1) followed by preparative HPLC to afford 3-(2-(4-bromophenyl)propan-2-yl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one. 1H NMR δ 7.45-7.26 (m, 7H), 6.78-6.73 (d, 2H), 4.81 (s, 1H), 4.59 (s, 1H), 3.33-3.27 (m, 1H), 3.05-2.95 (m, 1H), 2.60-2.44 (m, 3H), 2.28-2.18 (m, 1H), 1.65 (s, 3H), 1.59 (s, 3H), 1.41 (s, 3H).

Provenance & Evidence