Sodium Methoxide → HCID 57473829, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round bottom flask charged with 2-isopropyl-2-(2-oxo-2-(5-(trifluoromethyl)-2-(trii sopropylsilyloxy)benzylamino)-ethyl)pent-4-enoate (1.40 g, 2.57 mmol) in MeOH (26 mL) was cooled to 0° C. The solution was treated dropwise with sodium methoxide (25% solution in MeOH, 0.048 mL, 0.206 mmol) via syringe over 3 min, and the resulting mixture was stirred for 12 h. At this time mixture was diluted with EtOAc (100 mL) washed with brine (2×20 mL). The organic layer was dried (MgSO4) and concentrated on a rotary evaporator. The residue was purified using a 12 g silica gel cartridge and 20:1 Hex/EtOAc to 3:1 Hex/EtOAc to elute 3-allyl-3-isopropyl-1-(5-(trifluoromethyl)-2-(triisopropylsilyloxy)benzyl)pyrrolidine-2,5-dione (538 mg, 1.05 mmol, 41% yield) as a clear oil. LC/MS [M+H]+=512.12, HPLC tR=2.55 min [Waters Sunfire C18 4.6×50 mm column, 3 min gradient from 10/90/0.1 MeOH/H2O/TFA to 90/10/0.1 MeOH/H2O/TFA at 4 mL/min flow rate]. 1H-NMR (400 MHz, CDCl3) δ=7.38 (d, J=8.0 Hz, 1H), 7.14 (s, 1H), 6.88 (d, J=8.0 Hz, 1H), 5.67 (m, 1H), 5.19 (m, 2H), 4.75 (s, 2H), 2.56 (m, 2H), 2.35 (m, 1H), 2.17 (m, 2H), 1.16 (m, 2H), 0.98 (d, J=6.8 Hz, 3H), 0.92 (d, J=6.8 Hz, 3H).

Provenance & Evidence