Tributylstannane → HCID 86701263, compound

Participants

Reaction Steps

To a solution of (3S,6S,7R,8R)-8-(bromomethyl)-3-(tert-butoxycarbonylamino)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (238 mg, 0.51 mmol) in benzene (3 mL) was added Bu3SnH (178 mg, 0.61 mmol) and AIBN (2 mg) at room temperature (about 22° C.). The reaction solution was heated to reflux, stirred for 1 hr, and the solution was cooled to room temperature. The solvent was removed under vacuum and the residue was purified via column chromatography (SiO2, hexanes/EtOAc gradient) to afford the title compound (185 mg, 94%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 5.40-5.12 (m, 2H), 5.00 (t, J=9.8 Hz, 1H), 4.93-4.71 (m, 2H), 3.69-3.47 (m, 1H), 2.69-2.50 (m, 2H), 1.45 (s, J=4.7 Hz, 9H), 1.28 (d, J=6.3 Hz, 3H), 1.21 (dd, J=7.0, 1.2 Hz, 6H), 1.13 (d, J=6.7 Hz, 3H); ESIMS m/z 410 ([M+Na]+).

Provenance & Evidence