(1S)-1-(2,4-DIMETHOXYPHENYL)ETHANAMINE synthesis

Yield:1212264-50-0 33 %

Reaction Conditions:

with O,O'-dibenzoyl-D-tartaric acid in methanol;Heating;Resolution of racemate;

Steps:

(S)-1-(2,4-Dimethoxyphenyl)ethan-1-amine [(S)-1)].

A solution of 27.789 g (0.0739 mol, 1.01 equiv) of (-)-ODBTA in methanol (100 mL) in an Erlenmeyer flask was heated to the boiling point, and 13.244 g (0.0732 mol, 1 equiv) of racemic amine 1 was added dropwise. The flask was cooled to room temperature, the solution was decanted from needle-shaped crystals, 50 mL of methanol was added to the crystals, and the mixture was heated until complete dissolution. The solution was cooled to room temperature, and the precipitate was filtered off. Recrystallization from methanol was repeated two times, and the crystals were filtered off, dissolved in water, and treated with excess potassium hydroxide. The mixture was extracted with diethyl ether (3x100 mL), and the combined extracts were dried over sodium sulfate and evaporated. Yield 4.37 g (33%), colorless liquids. The spectral parameters of (S)-1 were similar to those of( R)-1. [α]D20 = -46.4° (neat), -25.6° (c = 1.0, CHCl3). Salt with (-)-ODBTA: [α]D20 = +87° (c = 0.2, MeOH).

References:

Barashkin;Polyakov;Shikut;Putilova;Gorovoy;Tafeenko;Zyk;Beloglazkina [Russian Journal of Organic Chemistry,2022,vol. 58,# 9,p. 1362 - 1367][Zh. Org. Khim.,2022,vol. 58,# 9,p. 1012 - 1018]