Benzenesulfinic acid, sodium salt → tert-butyl 3-(acetoxymethyl)-6-chloro-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

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Reaction Steps

The product from step J and sodium benzenesulfinate were coupled following the procedure of Example 29 step C. The crude product was purified by flash column chromatography (SiO2, 9:1 to 7:3, hexanes/ethyl acetate) to give tert-butyl 3-(acetoxymethyl)-6-chloro-8-(phenylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (110 mg, 84%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.98-7.95 (m, 3H), 7.86 (s, 1H), 7.58-7.49 (m, 3H), 5.10 (br s, 2H), 4.20-4.04 (m, 3H), 3.22-3.14 (m, 1H), 2.81 (d, J=17.4 Hz, 1H), 2.04 (s, 3H), 1.53 (s, 9H).

Provenance & Evidence