HCID 67588407, compound → HCID 44300540, compound

Participants

Reaction Steps

A mixture of 370 mg (0.55 mmol) 5-{(2R)-2-[[(2R)-2-(3-chloro-phenyl)-2-hydroxy-ethyl]-(2,2,2-trichloro-ethoxycarbonyl)-amino]-propyl}-benzo[1,3]dioxole-2,2-dicarboxylic acid diallyl ester, 10 mL glacial acetic acid and 357 mg (5.46 mmol) of Zn dust were stirred at room temperature for 40 h. The reaction mixture was filtered through celite, poured into 50 mL brine, and extracted with 3×50 mL EtOAc. The combined organics were washed with 3×75 mL sat. NaHCO3, 1×75 mL brine, dried over Na2SO4, filtered and evaporated to a colorless oil. Flash chromatography on silica gel, eluting with CHCl3 /MeOH (20/1 to 10/1), gave 180 mg (0.36 mmol, a 66% yield) of the title compound (Rf =0.35; 10/1 CHCl3 /MeOH) as a colorless gum; 1H NMR (300 MHz, CDCl3): δ 1.20-1.33 (m, 3H), 2.70-2.81 (m, 1H), 3.00-3.19 (m, 2H), 3.36-3.45 (m, 2H), 4.50-5.50 (br s, 2H), 4.70-4.80 (m, 4H), 5.10-5.20 (m, 1H), 5.25-5.40 (m, 4H), 5.82-6.00 (complex m, 2H), 6.70-6.91 (m, 3H), 7.17-7.30 (m, 3H), 7.41 (s, 1H); MS (ES) m/z (relative intensity): 502 (M+, 100).

Provenance & Evidence