(S)-2,2,2-trifluoro-N-(6-methoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetamide → tert-butyl (2S,3R)-4-((1S,3R)-3-(allyloxy)-6-isopropoxy-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate

Beteiligte Stoffe

Reaktionsschritte

Step AW (1): A solution of (1S,3R)-3-(allyloxy)-6-isopropoxy-2,3-dihydro-1H-inden-1-amine (1.3 g, 5.3 mmol), (S)-(1-oxiranyl-2-phenylethyl)-carbamic acid tert-butyl ester (1.7 g, 6.5 mmol), and lithium perchlorate (2.8 g, 26.3 mmol) in 40 mL CH3CN was stirred at 50° C. for 18 h. The mixture was poured into brine/NaHCO3 solution, extracted with EtOAc (200 mL×2). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified using silica-gel column chromatography (30-80% EtOAc/Hexane) to afford 1.2 g (45% yield) of tert-butyl (2S,3R)-4-((1S,3R)-3-(allyloxy)-6-isopropoxy-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate. LC-MS (M+H)+=511.25. 1H NMR (300 MHz, CDCl3) δ 1.2-1.4 (m, 15H) 2.5-2.7 (m, 1H) 2.7-2.9 (m, 2H) 3.0-3.1 (m, 2H) 3.5-3.7 (m, 1H) 3.7-3.9 (m, 1H) 4.0-4.1 (m, 2H) 4.2-4.3 (m, 1H) 4.5-4.7 (m, 2H) 4.7-4.8 (m, 1H) 5.1-5.3 (m, 2H) 5.8-6.0 (m, 1H) 6.8-6.9 (m, 1H) 7.0-7.3 (m, 7H).

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