Synthesis
(R)-4-Amino-4-phenyl-1-butene (0.04 mol) was dissolved in 200 ml of methanol in a simple ozonolysis apparatus without gas recycling and was cooled to - 20℃. The ozone generator was fed continuously with air. A concentration of 20 g/m3 (ST. P.) of ozone was produced and was completely reactive in the ozonolysis apparatus. After the end of the ozonolysis, the reaction solution was added dropwise over the course of 10 min to 100 ml of an ice-cooled methanolic sodium borohydride solution (0.9 mol/l). The reaction solution was then warmed to room temperature, and 10 ml of water was added to decompose excess sodium borohydride. After the solvent had been distilled off, the residue was extracted several times with dichloromethane, and the combined organic phases were dried over sodium sulfate and filtered. After the solvent had been distilled off, 0.37 mol of (R)-1-Phenyl-3-propanolamine (melting point 73-74°C) was obtained in 99% enantiomeric excess (93% yield).
