HCID 86700500, compound → HCID 86700499, compound

Participants

Reaction Steps

In a three-neck round-bottom flask, a sample of 4 (3.63 g, 5.69 mmol) was dissolved in a solution of EtOH/THF (25/180 mL). Rainey nickel (˜100 mg) was added to the mixture, which was then degassed by the freeze-pump-thaw method and the flask was backfilled with anhydrous H2 gas. The reaction was stirred at room temperature under a constant H2 stream for two days and then filtered to remove the Rainey nickel The solvent was removed under reduced pressure. The residue was dissolved in diethyl ether and extracted with a 10% HCl solution (3×, 50 mL). The aqueous phase was washed with hexanes (3×50 mL) followed by addition of 2 M NaOH to a final pH of 10. The precipitated solid was extracted into dichloromethane (3×50 mL). The combined organics were dried with sodium sulfate and the volatiles removed under reduced pressure. The residue was then recrystallized from methanol yielding 2.53 g (81%) of 5 as a colorless crystalline solid. 1H NMR (CDCl3-d) δ ppm 1.14 (18 H, d, J=6.9 Hz), 1.19 (9 H, t, J=7.0 Hz), 3.09 (6 H, br. s.), 3.21 (3 H, spt, J=6.9 Hz), 3.38 (6 H, q, J=6.9 Hz), 6.26 (3 H, d, J=2.9 Hz), 6.37 (3 H, d, J=2.7 Hz), 6.51 (1 H, s). 13C-{1H} NMR, δ 15.5, 24.0, 26.3, 38.4, 69.4, 111.1, 115.2, 138.9, 141.6, 142.9, 147.3. Anal. calcd. for C34H49N3O3: C, 74.55; H, 9.02; N, 7.67. Found: C, 74.26; H, 9.24; N, 7.59.

Provenance & Evidence