Trimethyl phosphonoacetate → HCID 90408952, compound

Participants

Reaction Conditions

Reaction Steps

Trimethyl phosphonoacetate (47 mg, 0.26 mmol) and DBU (39 mg, 0.26 mmol) were successively added to a 0° C. solution of LiCl (11 mg; 0.26 mmol) in MeCN (0.6 mL) under argon. The reaction mixture was stirred at 0° C. for 30 min, after which a solution of 120A compound [4-(1-(3-phenoxy-phenyl)-2-oxabicyclo[2.2.2]octan-4-yl)butanal] (60 mg, 0.171 mmol) in MeCN (0.5 mL) was added. The reaction mixture was stirred at rt for 2 h, then was concentrated in vacuo. The residue was diluted with ether and successively washed with 1N aq. HCl, sat′d aq. NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was chromatographed (SiO2; continuous gradient of EtOAc/hexanes from 0 to 40%) to give the title compound as a white solid (65 mg, 89%). [MS+H]+=407, 1H NMR (400 MHz, CDCl3) δ 7.29-7.19 (m, 3H), 7.10-6.97 (m, 3H), 6.95-6.88 (m, 2H), 6.87-6.83 (m, 1H), 6.77 (ddd, J=8.0, 2.5, 0.9 Hz, 1H), 5.75 (dt, J=15.6, 1.5 Hz, 1H), 3.72 (s, 2H), 3.66 (s, 3H), 2.11 (qd, J=7.2, 1.5 Hz, 2H), 1.93 (dd, J=9.5, 5.3 Hz, 4H), 1.67-1.51 (m, 4H), 1.40-1.25 (m, 2H), 1.14-1.02 (m, 2H).

Provenance & Evidence