HCID 77230808, compound → HCID 86680502, compound

Participants

Reaction Steps

1-(2,6-Dichlorothieno[2,3-b]pyridin-5-yl)ethanone (3.6 g, 14.63 mmol) was dissolved in THF (100 mL) and ccoled to −55° C. in a dry ice/MeCN bath. To this solution was added a solution of (+)-dip-chloride(tm) (10.32 g, 32.2 mmol) in THF dropwise. The reaction was allowed to warm slowly to rt overnight and quenched by addition of 10 mL of acetone and 50 mL of 50% sat. Na2CO3. The reaction was stirred for 1 h and diluted with 400 mL of ethyl acetate. The organic layer was washed with 2×100 mL of 50% sat Na2CO3, 2×100 mL of water, and 2×100 mL of brine. The reaction was dried over MgSO4, filtered and concentrated. The residue was slurried in 100 mL water/200 mL hexanes for 3 h to form white ppt that was filtered and dried to afford (R)-1-(2,6-dichlorothieno[2,3-b]pyridin-5-yl)ethanol. Enantiomeric excess as determined by chiral HPLC was found to be =99%. 1H NMR (400 MHz, CDCl3) δ 8.19 (d, J=0.8 Hz, 1H), 7.14 (s, 1H), 5.32 (qdd, J=6.3, 3.5, 0.8 Hz, 1H), 2.07 (J=3.5 Hz, 1H), 1.56 (d, J=6.6 Hz, 3H) ppm.

Provenance & Evidence