Water → 4-[Dimethylaminomethyl]-cyclohexane-carbaldehyde

Temperature

0 °C

(Methoxymethyl)triphenylphosphonium chloride (25.7 g, 75 mmole) was suspended in absolute THF (100 ml) under argon, potassium tert-butylate (8.42 g, 75 mmole) dissolved in absolute THF (70 ml) was added dropwise, and then stirred for 15 minutes at 0° C. The corresponding 4-[dimethylaminomethyl]-cyclohexanone 8 (50 mmole), dissolved in absolute THF (75 ml), was then added dropwise to the above solution and stirred overnight at RT. The mixture was hydrolysed by adding dropwise water (38 ml) and 6N HCL 112 ml) while cooling with iced water. After stirring for one hour at RT the mixture was extracted with ether (10×50 ml), the aqueous phase was adjusted to pH 11 with 5N NaOH, shaken with ethyl acetate (3×50 ml), dried over Na2SO4, and concentrated by evaporation in vacuo. The crude product was purified by flash chromatography with ethyl acetate/cyclohexane (1:1). As a rule two diastereomers were obtained in different ratios.

1. additionwas added dropwise
2. additionwas then added dropwise to the above solution
3. stirringstirred overnight at RT
4. stirringAfter stirring for one hour at RT the mixture
5. extractionwas extracted with ether (10×50 ml)
6. stirringshaken with ethyl acetate (3×50 ml)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated by evaporation in vacuo
9. customThe crude product was purified by flash chromatography with ethyl acetate/cyclohexane (1:1)
10. customAs a rule two diastereomers were obtained in different ratios

ORD record

ord-bc612dc3b5e34a4491165424b9751861

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728028B2