Ethanolamine → 2-[2-Benzyloxycarbonylamino-2-(methyl)propionylamino]ethanol

To a solution of 2-benzyloxycarbonylamino-2-(methyl)propionic acid (1 g) in tetrahydrofuran (5 mL) was added 1,1′-carbonylbis-1H-imidazole (889 mg), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 2-aminoethanol (0.38 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1) to give 2-[2-benzyloxycarbonylamino-2-(methyl)propionylamino]ethanol (973 mg). This material was dissolved in methanol (5 mL). To the solution was added 10% palladium-carbon powder (200 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give the title compound (505 mg).

1. stirringthe mixture was stirred at room temperature for 2 hours
2. customThe reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1)

ORD record

ord-8c7dc730e87347978f022c1974e072e1

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324176B2