Triethylamine → (S)-3-(t-butyldimethylsilyloxy)5bromo-1-phenyl pentane

Temperatur

0 °C

(S)-3-(t-butyldimethylsilyloxy)-5-phenyl-pentan-1-ol (10.6 g, 36 mmol) was dissolved in dichloromethane (80 ml), triethylamine (12.6 ml, 90.5 mmol) was added, and the mixture was cooled to 0° C. Methane sulfonyl chloride (4.2 ml, 54.3 mmol) was slowly added dropwise and the resulting mixture was stirred for 12 hours. After completion of the reaction, the reaction mixture was diluted with water (50 ml). The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 ml×2). The organic layers were combined, washed with saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated. Without further purification, the residue was dissolved in THF (60 ml). LiBr (7.86 g, 90.5 mmol) was added thereto and the mixture was refluxed for 4 hours. After completion of the reaction, water (80 ml) was added to the reaction solution which was then extracted with diethylether. The organic layers were combined, washed with saturated aqueous NaCl solution, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give colorless and transparent (S)-3-(t-butyldimethylsilyloxy)5-bromo-1-phenyl pentane (11 g, Yield 86%).

1. customAfter completion of the reaction
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with dichloromethane (50 ml×2)
4. washwashed with saturated aqueous NaCl solution
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customWithout further purification
9. dissolutionthe residue was dissolved in THF (60 ml)
10. temperaturethe mixture was refluxed for 4 hours
11. additionwas added to the reaction solution which
12. extractionwas then extracted with diethylether
13. washwashed with saturated aqueous NaCl solution
14. dry with materialdried over MgSO4
15. filtrationfiltered
16. concentrationconcentrated
17. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)
18. customto give colorless

ORD-Eintrag

ord-8d1f13263ef24af1874e9db2b2b591e5

Quelldatensatz

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06989458B2