Sodium hydride → HCID 49850061, compound

Participants

Reaction Steps

To a stirred solution of methyl 4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl(3-hydroxy-5-methyl-3-phenylhex-5-enyl)carbamate (35 mg, 0.03 mmol) in dry THF (2 mL) was added 60% NaH in oil (5 mg, 0.12 mmol). The mixture was heated at 60 C for 3 h, cooled, diluted with EtOAc (90 mL), washed with water (10 mL) and brine (10 mL), and dried over Na2SO4. Removal of the solvent left an oil (18 mg) which was purified by prep HPLC to afford 3-(4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl)-6-(2-methylallyl)-6-phenyl-1,3-oxazinan-2-one (17.7 mg, 55%) as an oil. LC-MS Method 1 tR=2.22 min, m/z=392; 1H NMR (CDCl3) δ 1.63 (s, 3H), 1.66 (s, 3H), 1.81 (s, 3H), 2.24 (m, 1H), 2.37 (m, 1H), 2.58 (m, 2H), 3.06 (m, 1H), 3.64 (m, 1H), 4.64 (s, 1H), 4.83 (s, 1H), 6.98 (m, 2H), 7.25-7.40 (7H).

Provenance & Evidence