Chlorotrimethylsilane → 2-(1,3-Diphenyl-1H-1,2,4-triazol-5-yl)ethanamine

To lithium borohydride (2M solution in THF, 899 μL, 1.8 mmol) was added dropwise trimethylchlorosilane (391 mg, 460 μL, 3.6 mmol) over a period of 5 min at 0-5° C., followed by the dropwise addition of a solution of 2-(1,3-diphenyl-1H-1,2,4-triazol-5-yl)acetonitrile (117 mg, 449 μmol) in THF (1.5 mL). The ice bath was removed after 10 min and the mixture was stirred at 60° C. for 1.5 h. The reaction mixture was cooled to 0-5° C. and 1 mL MeOH was added slowly (bubbling!). After 10 min the ice bath was removed and the mixture was allowed to warm up to RT. The mixture was poured into NaOH (1M aqueous solution, 15 mL) and extracted with dichloromethane (3×50 mL). The combined organic phase was dried over MgSO4, filtered and evaporated to give the product (118 mg with 90% purity, 402 μmol, 89.4%) as yellow viscous oil which was used without further purification.

1. customThe ice bath was removed after 10 min
2. temperatureThe reaction mixture was cooled to 0-5° C.
3. addition1 mL MeOH was added slowly
4. custom(bubbling!)
5. customAfter 10 min the ice bath was removed
6. temperatureto warm up to RT
7. additionThe mixture was poured into NaOH (1M aqueous solution, 15 mL)
8. extractionextracted with dichloromethane (3×50 mL)
9. dry with materialThe combined organic phase was dried over MgSO4
10. filtrationfiltered
11. customevaporated
12. customto give the product (118 mg with 90% purity, 402 μmol, 89.4%) as yellow viscous oil which
13. customwas used without further purification

ORD-Eintrag

ord-667f7f8b65d646d4a0553b5ace66d78b

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08772510B2