3-Thiomorpholineacetic acid, methyl ester synthesis

Yield:171351-30-7 56%

Reaction Conditions:

with triethylamine in chloroform; for 5 h;

Steps:

12.a

To a solution of 2-aminoethanethiol hydrochloride (2.0 g, 17.6 mmol) and triethylamine (8.6 mL, 61.7 mmol) in chloroform (20 mL) was added methyl 4-bromocrotonate (3.20 g, 17.8 mmol). After stirring for 5 hr, the reaction was partitioned between methylene chloride (20 mL) and brine (25 mL). The layers were separated and the organic layer was dried and concentrated. The remaining residue was purified by silica gel chromatography (50% ethyl acetate/hexanes) to give the desired product (1.72 g, 56%).

References:

US2004/72802,2004,A1 Location in patent:Page/Page column 44