Hydrochloric Acid → HCID 89705109, compound

Participants

Reaction Steps

To a stirred solution of the N-(2-oxo-2-((2R)-2-((3aS,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)pyrrolidin-1-yl)ethyl)quinoline-4-carboxamide (0.27 g, 0.585 mmol) in water (8 mL) at pH=3 (adjusting as necessary with 2N aq HCl) was added phenylboric acid (0.143 g, 1.17 mmol) and methyl-tert-butylether (7 mL). The mixture was stirred for 2 days (pH was 4) water and organic layer were separated, the water layer was adjusted to pH 3, and the water layer was extracted with a mixture 4-1 of DCM-isopropanol. The DCM layer was dried over sodium sulfate, filtrated evaporated and further purified using column chromatography (DCM-MeOH 0-10% MeOH) to yield a clear oil of 0.119 g (79%) (R)-1-(2-(quinoline-4-carboxamido)acetyl)pyrrolidin-2-ylboronic acid.

Provenance & Evidence