Apremilast synthesis

Yield:-

Reaction Conditions:

with trimethylsilyl iodide in dichloromethane at 20; for 24 h;

Steps:

5.7

5.7 (S)-4-Amino-2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-isoindole-1,3-dione To a stirred solution of (S)-4-amino-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-isoindole-1,3-dione (1 mmol) in anhydrous CH₂Cl₂ (20 mL), is added iodotrimethylsilane (6 mmol). The mixture is stirred at room temperature for 24 hours. The reaction mixture is diluted with brine and is extracted with CH₂Cl₁). The solvent is removed in vacuo to afford crude (S)-4-amino-2-[1-(3-ethoxy-4-hydroxy-phenyl)-2-methanesulfonyl-ethyl]-isoindole-1,3-dione. The product is purified by recrystallization.

References:

US2012/178708,2012,A1 Location in patent:Page/Page column 20