Benzylamine → HCID 11781347, compound

Participants

Reaction Conditions

Reaction Steps

To 18,6 g (0.10 mol) of the (2S,3R)-2,3-epoxydecanoic acid (V-2) obtained in (4) above were added 100 ml of water and 150 mg (0.37 mmol) of a phase transfer catalyst "Aliquat 336" (methyltri-n-octylammonium chloride produced by Henckels; hereinafter the same) at room temperature. The mixture was stirred at 2 to 3° C., and 32.1 g (0.30 mol) of benzylamine (VI) was added thereto dropwise, followed by stirring for about 5 minutes. To the mixture was further added 16 ml (0.08 mol) of a 5N sodium hydroxide aqueous solution, followed by refluxing for 2 hours and then stirring at room temperature for 16 hours. The reaction mixture was cooled to 0 to 5° C., 4 ml (0.02 mol) of a 5N sodium hydroxide aqueous solution was added, and the mixture was washed with two 100 ml portions of diisopropyl ether. The aqueous layer was adjusted to pH 5 to 6 by addition of 2N hydrochloric acid aqueous solution while stirring. The precipitated white crystals were washed with water and dried to give 26.7 g (0.091 mol; yield: 91.0%) of the title compound (III) (melting point: 197-199° C.).

Provenance & Evidence