Reaktion #48336

Reaktionsgleichung

(4S)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-amine

tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate

→

title compound

tert-Butyl (2S,3R)-4-((4S)-6-bromo-2-methyl-2-(trifluoromethyl)-3,4-dihydro-2H-chromen-4-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate

TFA

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 16 h
3. 3
   workup.WAITleft
4. 4
   Temperaturto reflux for 6 h
5. 5
   EinengenThe resulted mixture was concentrated
6. 6
   Sonstigepurified on Shimadzu HPLC

Vorschrift

A mixture of (4S)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-amine (179 mg, 577 μmol) and tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (198 mg, 750 μmol) in ethanol was heated at reflux for 16 h. At this point, there was still the starting amine left. An additional 1.3 eq of epoxide was added to the reaction, and continued to reflux for 6 h. The resulted mixture was concentrated and purified on Shimadzu HPLC to afford the title compound as a TFA salt. MS m/z: 573, 575.

Quelle