HCID 11150194, compound → HCID 11041684, compound

Temperature

-78 °C

The solution of the ester 4c (4.01 g, 14.3 mmol) in methylene chloride (100 mL) was cooled to -78° C. and diisobutylaluminium hydride (16.0 g, 11.2 mmol) was added dropwise to the solution. The reaction mixture was stirred at -78° C. for 1.5 h and it was quenched with methanol (30 mL) followed by addition of saturated aqueous ammonium chloride solution (50 mL). The mixture was then warmed slowly to room temperature. The solid was filtered and washed with methylene chloride (3×50 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by MPLC to give the alcohol 5 (2.71 g, 97%) as a white solid (mp=37.0°-38.0° C.).

1. customit was quenched with methanol (30 mL)
2. additionfollowed by addition of saturated aqueous ammonium chloride solution (50 mL)
3. temperatureThe mixture was then warmed slowly to room temperature
4. filtrationThe solid was filtered
5. washwashed with methylene chloride (3×50 mL)
6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by MPLC

ORD record

ord-13dd4b2eb26e46b3b50958c0fb6cbfa3

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05677467