N,N-Diethyl-2,2,2-trifluoroacetamide → HCID 68071560, Verbindung

Temperatur

-78 °C

tert-Butyl 1-(4-bromophenyl)ethylcarbamate (6.35 g, 21.2 mmol) was dissolved in dry THF (100 ml) and cooled to −78° C. under an atmosphere of nitrogen. n-Butyllithium (21 ml, 52.9 mmol, 2.5M in hexanes) was added dropwise under 10 minutes and the reaction was stirred at −78° C. for 3 hours. A solution of diethyl trifluoroacetamide (5.0 g, 29.6 mmol) in 10 ml dry THF was added dropwise and the reaction was stirred 1.5 hours at −78° C. Reaction was quenched with NH4Cl (sat) (50 ml) and H2O (50 ml) and allowed to reach room temperature. The aqueous phase was separated and extracted with EtOAc (100 ml). The combined organics were washed with NH4Cl (sat) (2*100 ml), H2O (100 ml), dried over MgSO4, filtered and evaporated. Unreacted starting material was removed by precipitation from MeOH/H2O (9/1). The mother liquor was evaporated and the residue purified by flash chromatography using Pet. Ether/EtOAc (7:1→5:1) as eluent to give 3.09 g (46%) of the title compound as white solids.

1. stirringthe reaction was stirred 1.5 hours at −78° C
2. customReaction
3. customwas quenched with NH4Cl (sat) (50 ml) and H2O (50 ml)
4. customto reach room temperature
5. customThe aqueous phase was separated
6. extractionextracted with EtOAc (100 ml)
7. washThe combined organics were washed with NH4Cl (sat) (2*100 ml), H2O (100 ml)
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customevaporated
11. customwas removed by precipitation from MeOH/H2O (9/1)
12. customThe mother liquor was evaporated
13. customthe residue purified by flash chromatography

ORD-Eintrag

ord-496dc8c8d91a4722ba9767de7dd1ea91

Quelldatensatz

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08415333B2