Hydrochloric Acid → HCID 60015351, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of iron(III) oxalate hexahydrate (148.2 mg, 0.31 mmol, 30 equiv) in H2O (41 mL) was cooled to 0° C. and air was bubbled through the mixture for 10 minutes. A solution of 10′-bromoanhydro-vinblastine (17a, 8.9 mg, 0.010 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 (7.7 mg, 0.20 mmol, 20 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′-bromo-vinblastine (17b, 2.0 mg, 0.0022 mmol, 22%) and 10′-bromoleurosidine (1.3 mg, 0.0015 mmol, 14%).

Provenance & Evidence