Reaction #48336

Reaction equation

(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

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 16 h
3. 3
   workup.WAITleft
4. 4
   Temperatureto reflux for 6 h
5. 5
   ConcentrationThe resulted mixture was concentrated
6. 6
   Otherpurified on Shimadzu HPLC

Procedure

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