Sodium hydride → (E)-butoxyimino-[(2S)-2-[[(3S)-3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl]oxycarbonyloxymethyl]pyrrolidin-1-yl]-oxidoazanium

Participants

Reaction Steps

To a solution of (3S)-3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridine-7-ol (900 mg, 3.44 mmol) in DMF (10 mL) at 0° C. was added sodium hydride (206 mg, 5.16 mmol) and, in 10 minutes, followed by addition of {(2S)-1-[(Z)-butoxy-NNO-azoxy]pyrrolidin-2-yl}methyl 1-chloroethyl carbonate (1.3 g, 4.02 mmol). After stirring at rt for 3 h, the mixture was partitioned between Et2O (50 mL) and water (50 mL). The organic layer was washed with brine (3×50 mL), dried over MgSO4, and concentrated. The residue was purified by flash chromatography (Biotage 25+M) using 30-50% EtOAc/hexane gradient, affording the title compound: 1H NMR (500 MHz, CDCl3) δ 8.08 (s, 1H), 7.37-7.27 (m, 4H), 6.21 (s, 1H), 5.29-5.13 (m, 2H), 4.49 (m, 1H), 4.40 (m, 1H), 4.35 (m, 1H), 4.20 (m, 2H), 3.65 (m, 1H), 3.57 (m, 1H), 2.52 (s, 3H), 2.20 (m, 1H), 2.05 (m, 2H), 1.90 (m, 1H), 1.75 (m, 2H), 1.42 (m, 2H), 0.94 (m, 3H).

Provenance & Evidence