Water → 2-bromo-N-(5-methylhex-3-yn-5-yl)butyramide

Temperatur

5 °C

5-Amino-5-methylhex-3-yne hydrochloride (2.21 g) was dissolved in dry dichloromethane (50 ml) and cooled to 5° C. with stirring. 2-Bromobutyryl bromide (3.45 g) was added to the mixture and dry triethylamine (4.17 ml) was added dropwise while maintaining the reaction temperature between 8–15° C. by cooling during the addition. The suspension, which had formed during the reaction, was diluted with further dry dichloromethane (20 ml) and stirred at 5° C. for 0.5 hours. The mixture was allowed to warm to ambient temperature and stirred for a further 2 hours. The reaction was treated with water and extracted with dichloromethane. The organic phase was separated, washed with water (three times), dried over magnesium sulphate and evaporated under reduced pressure to give a brown oil. The oil was fractionated by chromatography (silica; hexane/diethyl ether, 1:1 by volume) to give the required product, as a pale yellow solid, 3.17 g, m.p. 53–55° C.

1. additionwas added dropwise
2. temperaturewhile maintaining the reaction temperature between 8–15° C.
3. temperatureby cooling during the addition
4. customThe suspension, which had formed during the reaction
5. stirringstirred at 5° C. for 0.5 hours
6. temperatureto warm to ambient temperature
7. stirringstirred for a further 2 hours
8. extractionextracted with dichloromethane
9. customThe organic phase was separated
10. washwashed with water (three times)
11. dry with materialdried over magnesium sulphate
12. customevaporated under reduced pressure
13. customto give a brown oil

ORD-Eintrag

ord-d7c5bd26e1644a5494df15002bbab2ca

Quelldatensatz

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07166621B2