Benzyl bromoacetate → HCID 10348881, compound

Participants

Reaction Conditions

Reaction Steps

Compound (9) (650 mg, 1.38 mmol) was dissolved in tetrahydrofuran (5 mL) and cooled to -78° C. The resulting reaction mixture was treated with 1.8 mL of a 1M solution of lithium bis (trimethylsilyl)amide in tetrahydrofuran and stirred for 20 min. At this time, benzyl 2-bromoacetate (437 μL, 2.76 mmol) was added, the reaction continued at -78° C. for 10 rain and then warmed to room temperature (removed dry ice/isopropanol bath). After the reaction mixture reached room temperature, 10% NH4Cl (aqueous) was added and the resulting mixture was extracted with ethyl acetate. The combined organic fractions were dried over anhydrous MgSO4, filtered and evaporated at reduced pressure. The residue was purified using flash chromatography (silica gel, 4×20 cm, 20- 40% ethyl acetate/hexane) to yield the title compound (11) (388 mg, 46%). Compound (21): 1H NMR (CDCl3) δ 1.05 (9H, s), 1.98-2.73 (5H, m), 2.90-3.23 (1H, m), 3.37-3.73 (1H, m), 3.77 (2H, t, J=6.8 Hz), 4.07-4.80 (2H, m), 5.03-5.27 (3H, m), 6.97-7.83 (20H, m); MS (DCI/NH4) m/e 618 (M+H)+ ; TLC Rf 0.47 (silica gel, 7:3 hexane:ethyl acetate).

Provenance & Evidence