Réaction #48336

Équation de réaction

(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

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat reflux for 16 h
3. 3
   workup.WAITleft
4. 4
   Températureto reflux for 6 h
5. 5
   ConcentrationThe resulted mixture was concentrated
6. 6
   Autrepurified on Shimadzu HPLC

Mode opératoire

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.

Source