Dimethylacetamide → HCID 13424839, compound

Participants

Reaction Steps

To a solution of (RS,SR)-1-(p-toluenesulfonyloxy)-2-hydroxy-3-(2-ethoxy-phenoxy)-3-phenyl-propane (4.3 g) in dimethylacetamide (125 ml), 30% aqueous ammonia (125 ml) was added and the reaction mixture was kept for 12 hours at room temperature in an hermetically sealed vessel. The mixture was then concentrated under vacuum to a small volume, poured into water, saturated with NaCl, and extracted with ethylacetate. The organic phase was washed with water, dried over Na2SO4, filtered, and the solvent evaporated under vacuum. The obtained oily residue was purified on chromatographic column (CHCl3 :CH3OH:NH4OH 180:20:2 as eluant), to give 1,1 g of 1-amino-2-hydroxy-3-(2-ethoxy-phenoxy)-3-phenyl-propane as single RS,SR diastereoisomer, m.p. 115°-117° C. In analogous fashion, using appropriate starting compounds prepared according to the procedure described in the example 1, 2 and 7, the compound 1-amino-2-hydroxy-3-(4-trifluoromethyl-phenoxy)-3-phenyl-propane was obtained as single RS,SR diastereoisomer, m.p. 120°-122° C.

Provenance & Evidence