HCID 77230810, compound → HCID 86680500, compound

Participants

Reaction Conditions

Reaction Steps

In 30 mL of THF was dissolved (+)-dip-chloride(tm) (3.3 g, 10.2 mmol, 2.2 eq) and the resulting solution was cooled to −55° C. To this solution was added 1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethanone in 10 mL of THF via cannula, followed by a rinse with 10 mL of THF. The reaction was allowed to warm to RT slowly overnight and then quenched with 5 mL of acetone and 50% sat. Na2CO3. After stirring for 1 h, the reaction was diluted with ethyl acetate (100 mL) and transferred to a reparatory funnel. The organic layer was washed with 2×50 mL of 50% sat. Na2CO3, 2×50 mL of water, and 2×50 mL of brine. The organic layer was dried over MgSO4, filtered, and concentrated. Purification of the crude was achieved by slurrying in 20 mL water and 50 mL hexanes. The resulting solid was filtered and dried overnight to afford a pure white powder, (R)-1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethanol. Chiral HPLC (Chiralcel-AD, 30% isopropanol/hexanes)=92% ee. 1H NMR (400 MHz, CDCl3) δ 8.22 (s, 1H), 7.31 (s, 1H), 5.32 (dq, J=5.9, 3.5 Hz, 1H), 2.17 (d, J=3.5 Hz, 1H), 1.56 (d, J=6.3 Hz, 3H) ppm.

Provenance & Evidence