Реакция #48336

Уравнение реакции

(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

Растворители

ethanol

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux for 16 h
3. 3
   workup.WAITleft
4. 4
   Температураto reflux for 6 h
5. 5
   КонцентрированиеThe resulted mixture was concentrated
6. 6
   Другоеpurified on Shimadzu HPLC

Методика

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.

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