(1S,2R)-(-)-1-Amino-2-indanol → (R)-2-Benzyl-2,4-dihydroxy-N-((1S,2R)-2-hydroxy-indan-1-yl)-butyramide

Participants

Reaction Conditions

Reaction Steps

3-Benzyl-3-hydroxy-dihydro-furan-2-one (21c) (0.5 g, 2.6 mmol) and 2-hyroxypyridine (0.27 g, 2.8 mmol) in dry dichloromethane (15 mL) was added (1S,2R)-(−)-cis-1-amino-2-indanol (0.43 g, 2.8 mmol). The reaction mixture was stirred at 50° C. for 24 h and then evaporated. The residue was dissolved in ethyl acetate (80 mL) and washed with 1M HCl (20 mL), followed by saturated aqueous NaHCO3 (20 mL), and thereafter dried, filtered, and concentrated. The residue purified by silica gel flash chromatography using petroleum ether:acetone (3:1) gave 0.26 g of first eluted (compound 21d-(S)) and 0.33 g of second eluted (compound 21d-(R)) together in 66% yield of the title compounds.

Provenance & Evidence