Methanol → HCID 86749410, compound

A solution of (E)-7-[4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinyl]-5-hydroxy-3-oxo-6-heptenoic acid, methyl ester (235 mg, 0.54 mmol) in THF (8 ml) was treated with triethylborane (1.0M in THF, 1.13 ml, 1.13 mmol). Twenty milliliters of air was bubbled through the solution and the mixture was stirred at room temperature for 25 minutes. The solution was cooled to -78° C. and treated with NaBH4 (20.7 mg, 0.55 mmol) followed by dropwise addition of dry methanol (1.25 ml). After stirring at -78° C. for 1.5 hours, the mixture was quenched with 30% H2O2 (3.5 ml) in H2O (8 ml). The mixture was kept at -78° C. for 15 minutes, then warmed to room temperature and stirred for 30 minutes. The solution was poured into 50% saturated NaHCO3 and extracted with Et2O (3×). The combined Et2O extracts were washed with H2O, saturated NaHCO3 and brine, then dried (Na2SO4), filtered and stripped. Purification of the resulting oil (Flash, Merck SiO2, 70% EtOAc/30% hexane) gave (3R*, 5S*, 6E)-7-[4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinyl]-3,5-dihydroxy-6-heptenoic acid, methyl ester (188 mg, 80%) as a colorless oily foam.

1. customTwenty milliliters of air was bubbled through the solution
2. temperatureThe solution was cooled to -78° C.
3. stirringAfter stirring at -78° C. for 1.5 hours
4. customthe mixture was quenched with 30% H2O2 (3.5 ml) in H2O (8 ml)
5. waitThe mixture was kept at -78° C. for 15 minutes
6. temperaturewarmed to room temperature
7. stirringstirred for 30 minutes
8. additionThe solution was poured into 50% saturated NaHCO3
9. extractionextracted with Et2O (3×)
10. washThe combined Et2O extracts were washed with H2O, saturated NaHCO3 and brine
11. dry with materialdried (Na2SO4)
12. filtrationfiltered
13. customPurification of the resulting oil (Flash, Merck SiO2, 70% EtOAc/30% hexane)

ORD record

ord-abf8afbde6c74b168556c5c3a1fd9a50

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05686433