Water → HCID 50905520, compound

Participants

Reaction Steps

A stirred solution of crude 3-(4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl)-6-((2-methyloxiran-2-yl)methyl)-6-phenyl-1,3-oxazinan-2-one (18 mg, ≦0.038 mmol) in dry THF (2 mL) was cooled in an ice bath and 1 M LiEt3BH in THF (0.2 mL, 0.2 mmol) was added. The mixture was stirred in the ice bath for 3 h and 30% H2O (1 mL) and water (5 mL) were added. The mixture was diluted with EtOAc (90 mL), washed with brine (10 mL), 30% aq Na2S2O3 (10 mL) and brine (10 mL), and dried over Na2SO4. Removal of the solvent left an oil (17 mg) which was purified by prep HPLC to afford 3-(4-(4-fluorophenyl)-2-methylbut-3-yn-2-yl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (6.9 mg) as an oil. LC-MS Method 1 tR=1.90 min, m/z=; 1H NMR (CDCl3) δ 1.06 (s, 3H), 1.19 (s, 3H), 1.74 (s, 3H), 1.80 (s, 3H), 2.23 (s, 2H), 2.32 (m, 2H), 2.65 (br s, 1H), 2.91 (m, 1H), 3.62 (m, 1H), 6.97 (m, 2H), 7.25-7.45 (7H).

Provenance & Evidence