Water → 3-Hydroxy-5-chloropyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of crude (R)-tert-butyl 2-((5-chloropyridin-3-yloxy)methyl)pyrrolidine-1-carboxylate (5.15 g, Ca. 11.28 mmol, EXAMPLE 29 Step 1) and sodium bicarbonate (2.77 g, 32.9 mmol) in dichloromethane was added m-chloroperbenzoic acid (mCPBA) (4.26 g, 24.7 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min, and the mixture was warmed to room temperature during 30 min period. After being stirred at room temperature for 6 h, water was added to the mixture. The mixture was extracted with dichloromethane twice and washed with aq. sodium thiosulfate and brine. The extracts were combined and dried over sodium sulfate and concentrated in vacuo to afford an oil. The residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 7:3 to ethyl acetate) to afford 2.709 g (73% from 5-chloropyridin-3-ol) of the title compound as a colorless viscous oil.

Provenance & Evidence