Hydrochloric Acid → {4-[Dimethylamino-(3-fluorophenyl)-methyl]-cyclohexyl}-acetaldehyde

温度

0 °C

(Methoxymethyl)triphenylphosphonium chloride (26.73 g, 78 mmole) was suspended in absolute THF (90 ml) under argon, potassium tert-butylate (8.75 g, 78 mmole), dissolved in absolute THF (90 ml), was added dropwise at 0° C., and the mixture was then stirred for 15 minutes at 0° C. The aldehyde 9b (13.69 g, 52 mmole), dissolved in absolute THF (90 ml), was then added dropwise at RT and the mixture was stirred overnight at RT. The mixture was hydrolysed by dropwise addition of water (50 ml) and 6N HCl (150 ml), while cooling with iced water. After stirring for one hour at RT the mixture was extracted 10 times with ether (each time 50 ml). The aqueous phase was adjusted to pH 11 with 5N NaOH, shaken three times with ethyl acetate (each time 100 ml), dried over Na2 SO4 and concentrated by evaporation in vacuo. The crude product was purified by flash chromatography with ethyl acetate/cyclohexane (1:1).

1. additionwas added dropwise at 0° C.
2. additionwas then added dropwise at RT
3. stirringthe mixture was stirred overnight at RT
4. stirringAfter stirring for one hour at RT the mixture
5. extractionwas extracted 10 times with ether (each time 50 ml)
6. stirringshaken three times with ethyl acetate (each time 100 ml),
7. customdried over Na2 SO4
8. concentrationconcentrated by evaporation in vacuo
9. customThe crude product was purified by flash chromatography with ethyl acetate/cyclohexane (1:1)

ORDレコード

ord-cd99407096e045d89a559822721c434e

出典データセット

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07728028B2