Water → HCID 15572608, compound

Participants

Reaction Steps

To a suspension of 0.55 g of LiAlH4 in 18 ml of anhydrous tetrahydrofuran there was added dropwise at 30° C. over 4 hours 1 g of 2-hydroxy-1-nitro-3-phenyl-3-(2-methoxy-phenoxy)-propane sodium salt in 70 ml of anhydrous tetrahydrofuran. After the addition, the mixture was cooled and decomposed with water, 15% NaOH, water. It was then filtered; the solid was washed with tetrahydrofuran and the solvent evaporated to dryness. The residue was dissolved in ethyl ether and extracted with 3% HCl, made alkaline with 20% NaOH NaOH and re-extracted with ethyl ether. The organic solution was then washed with water, dried over Na2SO4, filtered and evaporated to dryness. A small quantity of isopropyl ether was then used to ground it to obtain 2-hydroxy-3-(2-methoxy-phenoxy)-3-phenyl-propylamine (0.4 g); melting point 84°-110° C. (R=47.2%) as mixture of two diasteroisomers. The mixture was separated by column chromatography on silica gel (phase: CHCl3 /CH 3 OH/32% NH4OH-150/50/2) to obtain two distinct diastereoisomers having melting point of 126°-129° C. (diastereoisomer with Rf<) and 105°-110° C. respectively (diastereoisomer with Rf>).

Provenance & Evidence