Lithium Chloride → HCID 89996240, compound

Participants

Reaction Steps

To a stirred solution of (2-chloro-5-iodo-pyridin-4-yl)-methanol (2 g, 7.44 mmol, 1 eq) in dry THF (20 mL) was added i-PrMgCl.LiCl complex (1.3M in THF, 13.7 mL, 17.8 mmol, 2.4 eq) at −20° C. in drop wise manner over period of 10 minutes. Pre-dissolved solution of N-boc-3-azetidinone (1.53 g, 8.9 mmol, 1.2 eq) in dry THF (10 mL) was added at −20° C. to above reaction mixture. Resulting reaction mixture was stirred at room temperature for 16 hours under nitrogen atmosphere. After maximum consumption of starting material, reaction mixture was cooled to 0° C., quenched with 10% citric acid solution (20 mL) and extracted with ethyl acetate (3×50 mL). Combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure to get brown oil (2.2 g, crude). Crude compound was purified by column chromatography by using silica gel (100-200 mesh). Desired compound was eluted at 20% ethyl acetate in hexane to afford title compound as yellow solid (0.45 g, 19%). 1H NMR (400 MHz, CDCl3) δ: 1.38 (s, 9H), 3.96 (d, J=8.8 Hz, 2H), 4.38 (d, J=9.32 Hz, 2H), 4.53 (d, J=5.64 Hz, 2H), 5.53 (t, J=5.32 Hz, 1H), 6.40 (s, 1H), 7.57 (s, 1H), 8.33 (s, 1H). LC-MS (m/z): 314.9 (M+H).

Provenance & Evidence