Hydrochloric Acid → HCID 85657726, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the oxime from Step 3 (400 mg, 1.52 mmole) in EtOH (7 mL) at 0° C. there was added pyridine-borane complex (288.5 mg, 3.10 mmole) and 4M ethanolic HCl (1.16 mL, 4.65 mmol). The mixture was stirred at 0° C. for 20 minutes, then allowed to warm up to r.t. Most of the EtOH was evaporated away, H2O (20 mL) and 1N aqueous HCl (10 mL) was added, and the mixture was extracted twice with Et2O. The aqueous fraction was then made basic with 2.5N aqueous NaOH, and extracted twice with Et2O. From these extracts a crude product was obtained which was purified by chromatography on silica gel, eluting with 5% EtOH in CH2Cl2 to afford the title product as a colorless oil.

Provenance & Evidence