Hydrochloric Acid → HCID 71450169, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of iron(III) oxalate hexahydrate (60.4 mg, 0.125 mmol, 10 equiv) in H2O (50 mL) was stirred 2 hours. The reaction mixture was cooled to 0° C. and air was bubbled through the mixture for 10 minutes. A solution of 10′-fluoroanhydrovinblastine (19a, 10.1 mg, 0.0125 mmol, 1 equiv) in H2O (0.5 mL), aqueous 0.1 N HCl (0.5 mL), and CF3CH2OH (0.1 mL) was transferred by pipette to the mixture and NaBH4 (9.5 mg, 0.25 mmol, 1 equiv) in H2O (1 mL) was added to the mixture at 0° C. The resulting mixture was stirred for 30 minutes before being quenched by addition of 28-30% aqueous NH4OH (10 mL). The mixture was extracted with 10% MeOH in CH2Cl2 and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. PTLC (SiO2, Et3N:MeOH:EtOAc=3:3:97) provided 10′-fluorovinblastine 19b (4.0 mg, 0.0048 mmol, 39%) as a white solid and 10′-fluoroleurosidine (2.7 mg, 0.0033 mmol, 26%).

Provenance & Evidence