Magnesium perchlorate → 2-Hydroxy-3-(4-methoxyindolin-1-yl)-3-phenylpropanol

A solution of 1.00 g (6.62 mmol) of 4-methoxyindoline (Gangjee et al., J. Med. Chem. 1997, 40, 479-485) and 1.90 g (8.51 mmol) of magnesium perchlorate in 20 mL of CH3CN was treated in a dropwise manner with a solution of 1.00 g (6.62 mmol) of 2,3-epoxy-3-phenyl-1-propanol (Ogata and Tomizawa, Bull. Chim. Soc. Jap. 1977, 50, 261-265) in 10 mL of CH3CN. The reaction was stirred at ambient temperature for 2.5 hours and was diluted with 30 mL of saturated aqueous NaHCO3. The organic layer was separated and the aqueous phase was extracted with EtOAc (2×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The oil was purified by radial chromatography (SiO2; 10% then 20% then 30% EtOAc in hexanes) to afford 1.55 g (5.17 mmol; 78%) of the subtitled compound as a solid.

1. customThe organic layer was separated
2. extractionthe aqueous phase was extracted with EtOAc (2×20 mL)
3. dry with materialThe combined organic layers were dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe oil was purified by radial chromatography (SiO2

ORD-Eintrag

ord-fba1dbd9606b4768b5f2bb98b07bc2bb

Quelldatensatz

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06448284B1