(4-Benzylmorpholin-2-yl)methanamine → (S)-(4-benzylmorpholin-2-yl)methanamine
Reaction equation
[NH2:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1>C(O)C>[NH2:1][CH2:2][C@@H:3]1[O:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
(RS)-2-Aminomethyl-4-benzylmorpholine (326.1 g) was dissolved in ethanol (3 L) and dibenzoyl-D-tartaric monohydrate (535 g) was added. The mixture was refluxed for dissolution and then left standing at room temperature for 16 hours. The precipitated crystals were collected by filtration and recrystallized from a mixed solvent of ethanol:water=25:1. The obtained crystals were suspended in water (1.2 L) and aqueous sodium hydroxide solution was added with stirring to make the suspension basic, which was followed by extraction with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was distilled off to give 138.4 g of (S)-2-aminomethyl-4-benzylmorpholine as a colorless oil.