Isopropanol → HCID 59314341, compound

Participants

Reaction Steps

A 100 mL round bottom flask containing the 2-(2-hydroxy-3-methyl-benzylamino)-indan-2-carboxylic acid ethyl ester (364, 1.01 g, 3.10 mmol) is charged with dry tetrahydrofuran (THF, 10 mL). A stirring bar is added and stirring is initiated. After dissolution, iPrOH ([67-63-0], 0.47 mL, 6.21 mmol) and triphenylphosphine ([603-35-0], 1.63 g, 6.21 mmol) are added in turn. After dissolution of the triphenylphosphine, diisopropylazodicarboxylate (1.20 mL, 6.21 mmol) is added. The reaction flask is capped and allowed to stir at ambient temperature overnight. After 24 h, tlc analysis (silica, 1:2 EtOAc/Heptanes) indicates that the starting material is completely consumed and converted to a higher moving spot as visualized by UV. The stirring bar is removed from the reaction flask and the solvent removed under reduced pressure. Pumping to constant weight gives 2.06 g of viscous yellow oil. This is dissolved in DCM (10 mL) and applied to an ISCO Companion which had been fitted with a 40 g column (silica). The column is eluted with EtOAc/heptanes (5%) for 4 column volumes followed by a linear gradient to 60% EtOAc/heptanes over 10 column volumes and then 90% EtOAc/heptanes for 2 column volumes. 17 mL fractions of UV Active eluent are collected. Fractions 5-14 are combined and evaporated by pumping to constant weight to give viscous residue (0.42 g, 37%).

Provenance & Evidence