Hydrochloric Acid → 2,3-Dihydro-1-hydroxamino-1H-pyrrolo[1,2-a]indole

Participants

Reaction Conditions

Reaction Steps

To a suspension of the oxime from Step 1 (2.5 g, 13.4 mmol) in THF (30 mL) and EtOH (30 mL), at 0° C. there was added pyridine-borane complex (3.12 g, 33.6 mmol) and then, slowly, 12N aqueous HCl (3.9 mL, 47 mmol). The mixture was stirred at 0° C. for 15 minutes, then at r.t. for 20 hours. The solvents were evaporated and the residue dissolved in H2O (100 mL) and extracted with EtOAc (2×20 mL). The aqueous fraction was then brought to pH 8 with 2.5N aqueous NaOH and the precipitate filtered to afford the title compound as a white solid, m.p.: 159°-161° C.

Provenance & Evidence