Ethyl bromoacetate → HCID 70045577, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 36a (340 mg, 1.1 mmol) in THF (10 mL) at -78° C. was added NaN(TMS)2 (1.0M in THF, 1.1 mL). After 15 minutes ethyl bromoacetate (250 uL, 2.2 mmol) was added and the reaction mixture to warm to -20° C. After 2 hours the reaction was quenched with HOAc (0.1 mL) and then concentrated. Flash chromatography (silica gel, 50% ethyl acetate/hexanes) gave 37a (380 mg, 90%) as an oil. TLC Rf=0.66 (10% methanol/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 4.22 (q, J=7 Hz, 2H), 4.10 (m, 2H), 4.08 (s, 2H), 3.24 (m, 2H), 2.70 (m, 2H), 2.44 (m, 1H), 2.26 (m, 1H), 2.00-1.65 (m, 4H), 1.48 (s, 9H), 1.50-1.30 (m, 4H), 1.31 (t, J=7 Hz, 3H), 1.12 (m, 2H).

Provenance & Evidence