반응 #2492865

반응 방정식

(2S,3aS,7aS)-tert-butyl 2-((2-amino-4-bromophenyl)carbamoyl)octahydro-1H-indole-1-carboxylate

(2S,3aS,7aS)-tert-butyl 2-((2-amino-5-bromophenyl)carbamoyl)octahydro-1H-indole-1-carboxylate

→

(2S,3aS,7aS)-tert-butyl 2-(6-bromo-1H-benzo[d]imidazol-2-yl)octahydro-1H-indole-1-carboxylate

용매

acetic acid

반응 조건

후처리

1. 1
   기타were consumed (as judged by LC-MS analysis)
2. 2
   온도The reaction was cooled to rt
3. 3
   기타the solvent was removed under vacuum
4. 4
   workup.DISSOLUTIONThe remaining residue was dissolved in ethyl acetate (500 mL)
5. 5
   workup.ADDITIONaq ammonia (100 mL) was added carefully
6. 6
   workup.ADDITIONAdditional water (100 mL) was added
7. 7
   기타the organic layer was separated
8. 8
   기타collected
9. 9
   추출The aq phase was extracted with ethyl acetate (2×300 mL)
10. 10
    세척The combined organic phase was washed with water (200 mL)
11. 11
    건조dried over MgSO4
12. 12
    농축The solution was concentrated
13. 13
    기타the remaining residue was purified by silica gel column chromatography (hexanes/ethyl acetate)

실험 절차

An isomeric mixture (14) of (2S,3aS,7aS)-tert-butyl 2-((2-amino-4-bromophenyl)carbamoyl)octahydro-1H-indole-1-carboxylate and (2S,3aS,7aS)-tert-butyl 2-((2-amino-5-bromophenyl)carbamoyl)octahydro-1H-indole-1-carboxylate (160 g, 0.36 mol) was dissolved in acetic acid (480 mL) and the reaction mixture was stirred at 65° C. until the starting materials were consumed (as judged by LC-MS analysis). The reaction was cooled to rt and the solvent was removed under vacuum. The remaining residue was dissolved in ethyl acetate (500 mL) and aq ammonia (100 mL) was added carefully. Additional water (100 mL) was added and the organic layer was separated and collected. The aq phase was extracted with ethyl acetate (2×300 mL). The combined organic phase was washed with water (200 mL), followed by brine (200 mL), and dried over MgSO4. The solution was concentrated and the remaining residue was purified by silica gel column chromatography (hexanes/ethyl acetate) to afford (2S,3aS,7aS)-tert-butyl 2-(6-bromo-1H-benzo[d]imidazol-2-yl)octahydro-1H-indole-1-carboxylate (15) (140 g).

출처