Azido(trimethyl)stannane → HCID 178420043, compound

Participants

Reaction Conditions

Reaction Steps

Azidotrimethyltin (82.0 mg, 0.40 mmol) was added to a stirred solution of 6a (40.0 mg, 0.09 mmol) in toluene (0.6 mL) at room temperature and the resulting mixture heated to 140° C. After 72 h, the reaction mixture was cooled to room temperature, and the volatiles were removed in vacuo. The residue was taken up in cold hydrogen chloride/MeOH (1 mL; saturated solution) and stirred for 20 min at room temperature. The reaction mixture was concentrated in vacuo, and the crude residue was purified by flash chromatography on silica gel (gradient elution, 0-10% methanol/methylene chloride as eluent) to furnish the title compound as an off-white foam. Rf: 0.15 (1:2 hexane:EtOAc). m/z (ES) 474 (MH)+. 1H NMR (500 M, CDCl3): δ 0.89-0.93 (m, 1H), 1.19-1.26 (m, 1H), 1.26-1.40 (m, 2H), 1.46-1.55 (m, 1H), 1.72 (br d, 1H), 1.88 (td, J=2.8, 13.6 Hz, 1H), 2.03 (dd, J=2.3, 13.7 Hz, 1H), 2.34 (br s, 1H), 3.01 (br d, J=3.6 Hz, 1H), 5.55 (s, 2H), 6.94 (dd, J=2.3, 8.4 Hz, 1H), 7.0-7.22 (m, 3H), 7.22-7.32 (m, 3H), 7.62-7.68 (m, 2H), 7.78-7.86 (m, 2H), 7.90-7.96 (m, 1H), 8.20 (m, 1H), 8.37 (m, 1H).

Provenance & Evidence