1: With triethylamine in methanol; dichloromethane T=15 - 30°C; pH=9 - 9.5; 2: With acetic acid T=30°C; pH=4.0 - 4.5;

1: phosphate buffer / diethyl ether; tetrahydrofuran / 2 h / Ambient temperature 2: DMAP, Et3N / acetonitrile / 2 h / Ambient temperature 3: Bu3SnH, AIBN / toluene / 3 h / 100 °C 4: 84 percent / AcOH, TBAF / tetrahydrofuran / 0.25 h / Ambient temperature 5: 39 percent / AcOH / methanol / 120 h / Heating View Scheme

T=37°C; 2 h; Tris-HCl buffer (pH 9); other pH, time; chemical stability, epimerization and degradation of CNDAC; Product distribution;