Phthalimide → CPPHA

Participants

Reaction Conditions

Reaction Steps

Compound 1-3 (6.0 g 0.015 moles) was dissolved in 50 mL of DMF. To that pthalimide (3.31 g 0.023 moles), K2CO3 (6.2 g 0.045 moles) and a catalytic amount of KI were added and allowed to stir at 50° C. overnight. Upon completion the reaction was diluted with ethyl acetate and then washed with brine (6×25 mL's) to afford 2.9 grams of 1-4 in a crude mixture, which was then purified by normal phase chromatography. 1H NMR (300 MHz, CDCl3): 4.83 ppm (2H, S); 7.05 ppm (2H, m); 7.36 ppm (1H, dd, J=2.4 Hz, 8.6 Hz); 7.50 ppm (1H, dt, J=1.5 Hz, 8.5 Hz); 7.59 ppm (1H, d, J=2.4 Hz); 7.75 ppm (3H, m); 7.91 ppm (2H, m); 8.18 ppm (1H, d, 7.2 Hz); 10.17 ppm (1H, s); 12.27 ppm (1H,s) Analytical LCMS: single peak (214 nm) at 3.633 min (CH3CN/H2O/1% TFA, 4 min gradient), HRMS calc'd for C22H15N2O4Cl (M+H), 407.0799; found 407.0793 (M+H).

Provenance & Evidence