Propylene Oxide → HCID 68108948, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 8-bromo-6-iodo-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (200 mg, 0.42 mmol) in anhydrous THF (2 mL) at −78° C. was added isopropylmagnesium bromide (2 M solution in THF, 0.4 mL, 0.84 mmol). The reaction mixture was stirred at −40° C. for 1 h and Cu(I) iodide (96 mg, 0.50 mmol) was added. The reaction mixture was stirred at −40° C. for a further 30 min then 2-methyloxirane (0.29 mL, 4.18 mmol) was added. After 1 h, the reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 7:3 hexanes/ethyl acetate) to give tert-butyl 8-bromo-6-(2-hydroxypropyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (110 mg, 17%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 7.42 (d, J=1.5 Hz, 1H), 7.22 (d, J=1.5 Hz, 1H), 4.50 (s, 2H), 4.30-4.16 (m, 1H), 3.82 (br s, 2H), 3.05-2.91 (m, 2H), 2.85 (br s, 2H), 1.50 (s, 9H), 1.27 (d, J=6.3 Hz, 3H).

Provenance & Evidence