Water → HCID 67518168, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask charged with stirring bar, 1-tert-butyl 4-(9H-fluoren-9-ylmethyl) 2-hydroxypiperazine-1,4-dicarboxylate (4.34 g, 10.2 mmol) was dissolved in THF (100 mL) and was cooled down to 0° C. under N2. Then TFAA (1.589 mL, 11.25 mmol) was added. After stirring at 0° C. for 20 minutes, reaction was quenched by adding saturated aq. NaHCO3 and warmed up to room temperature. Then reaction was diluted by adding 200 mL of DCM and 100 mL of water. Layers were separated and aqueous layer was extracted with 100 mL of DCM. Organic phases were combined and dried over anhydrous Na2SO4. Removing solvent gave crude product that was purified by ISCO (120 gram silica gel column, 0-50% EtOAc/Hexane gradient). Concentration gave the title compound. 1H NMR (ppm) (500 MHz, CDCl3): δ 7.81 (2H, d, J=7.59 Hz), 7.61 (2H, dd, J=13.92, 7.51 Hz), 7.44 (2H, t, J=7.49 Hz), 7.35 (2H, t, J=7.47 Hz), 6.27-6.14 (2H, m), 4.52 (2H, dd, J=19.02, 6.70 Hz), 4.31 (1H, t, J=6.89 Hz), 3.81-3.68 (4H, m), 1.54 (9H, s); LC/MS (M+23)+=429.13;

Provenance & Evidence