Tyramine → Trifluoroacetate

Participants

Reaction Steps

A solution of pivaloyl-chloride (10.0 ml) was added dropwise to a stirred solution of tyramine (10.2 g) in a dichloromethane/trifluoroacetic acid mixture (1:1 v/v). The reaction mixture was stirred for 4 hours and the solvents then removed in vacuo. The syrupy residue was triturated with an ethyl acetate/diethyl ether mixture (3:1 v/v) to give 2-(4-pivaloyloxyphenyl)ethylamine as a colourless trifluoroacetate salt, m.p. 255°-257° C.; NMR: 1.3(s, 9H, pivaloyl-H), 2.85(m, 2H, CH2Ph), 3.05(m, 2H, CH2N), 7.05(d, 2H, phenyl-H), 7.3(d, 2H, phenyl-H), 8.0(broad s, 3H, NH3); m/e 222 (M+H)+.

Provenance & Evidence