Sodium hydride → 6-(2-methylallyl)-6-phenyl-3-(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)-1,3-oxazinan-2-one

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Reaction Steps

To a stirred solution of methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)carbamate (14 mg, 0.031 mmol) in dry THF (1 mL) was added 60% NaH in oil (10 mg, 0.25 mmol). The mixture was heated at 50 C in an oil bath for 1.5 h, cooled, diluted with 5% aq HCl (0.5 mL) and MeOH (0.5 mL) and purified by prep HPLC to afford the title compound (8.7 mg, 67%) as an oil. LC-MS Method 1 tR=1.90 min, m/z=417; 1H NMR (CDCl3) 1.58 (s, 3H), 1.76 (s, 6H), 2.25 (m, 1H), 2.36 (m, 1H), 2.56 (dd, 2H), 3.03 (m, 1H), 3.52 (m, 1H), 4.58 (s, 1H), 4.81 (s, 1H), 7.25-7.80 (11H).

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