Reacción #48336

Ecuación de reacción

(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

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux for 16 h
3. 3
   workup.WAITleft
4. 4
   Temperaturato reflux for 6 h
5. 5
   ConcentraciónThe resulted mixture was concentrated
6. 6
   Otropurified on Shimadzu HPLC

Procedimiento

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.

Fuente