HCID 10335383, compound → HCID 14986678, compound

To a solution of 4.17 g (13.8 mmol) of 5-hydroxy-8-(3-pyridyl)-1-(2-tetrahydropyranyloxy)-octane (example 37) in 30 ml dry dimethylformamide is added 17 ml (27.6 mmol) of a 1.61M solution of potassium t-butoxide in tetrahydrofuran and the resulting red solution is stirred for 0.5 h. Then the mixture is cooled to 10° and 4.9 g (30.4 mmol) of sodium bromoacetate is added followed by 40 ml dry dimethylformamide, and the reaction mixture is stirred at room temperature for 18 h. The reaction mixture is diluted with ether and water. The ether layer is separated and the aqueous phase is adjusted to pH=6.5 using 1N aqueous hydrochloric acid. The resulting solution is extracted thrice with ethyl acetate. The aqueous phase is again adjusted to pH=6.5 and extracted again. The combined organic phase is washed with brine, dried, filtered, and concentrated to give 8-hydroxy-4-[3-(3-pyridyl)propyl]-3-oxa-octanoic acid.

1. temperatureThen the mixture is cooled to 10°
2. stirringthe reaction mixture is stirred at room temperature for 18 h
3. customThe ether layer is separated
4. extractionThe resulting solution is extracted thrice with ethyl acetate
5. extractionextracted again
6. washThe combined organic phase is washed with brine
7. customdried
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-2d252ca7ac884cceaa34fe6eceaf288c

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05153214