Tert-butyl 2-(acetoxymethyl)-4-oxopiperidine-1-carboxylate → tert-butyl 3-(acetoxymethyl)-8-bromo-6-chloro-1,4,4a,9b-tetrahydrobenzofuro[3,2-c]pyridine-2(3H)-carboxylate

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Reaction Steps

The product obtained from step I (1.33 g, 4.9 mmol) was reacted with O-(4-bromo-2-chlorophenyl)hydroxylamine hydrochloride following the procedure of Example 29 step B. Purification by column chromatography (SiO2, 49:1 to 19:1 hexanes/ethyl acetate) afforded tert-butyl 3-(acetoxymethyl)-8-bromo-6-chloro-1,4,4a,9b-tetrahydrobenzofuro[3,2-c]pyridine-2(3H)-carboxylate (203 mg, 8%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 7.43 (s, 1H), 7.38 (d, J=1.8 Hz, 1H), 5.14 (br s, 2H), 4.10-4.07 (m, 3H), 3.16-3.14 (m, 1H), 2.80 (d, J=17.4 Hz, 1H), 2.04 (s, 3H), 1.52 (s, 9H).

Provenance & Evidence