Benzylethanolamine → (R)-1-(benzyl(2-hydroxyethyl)amino)propan-2-ol

To a solution of (2S)-2-hydroxypropyl 4-methylbenzenesulfonate (540 g, 2.34 mol) in EtOH (3 L) at 0° C. was added a solution of KOH (160 g, 2.5 mol) in ethanol (2 L). The mixture was maintained at room temperature overnight. Upon completion, 2-benzylamino-ethanol (500 g, 3.3 mol) was added to the reaction, and the resulting mixture was stirred at room temperature for two days. Boc2O (500 g, 2.29 mol) was then added and the mixture was stirred for another day. The mixture was then filtered, the filter cake washed with ethanol (500 mL), and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc (3.5 L), washed with water (500 mL) and brine (500 mL), and concentrated in vacuo. The resulting crude residue was purified by silica gel chromatography (1:2 EtOAc:petroleum ether) to afford the title compound as a brown oil.

1. stirringthe mixture was stirred for another day
2. filtrationThe mixture was then filtered
3. washthe filter cake washed with ethanol (500 mL)
4. concentrationthe filtrate concentrated in vacuo
5. dissolutionThe residue was dissolved in EtOAc (3.5 L)
6. washwashed with water (500 mL) and brine (500 mL)
7. concentrationconcentrated in vacuo
8. customThe resulting crude residue was purified by silica gel chromatography (1:2 EtOAc:petroleum ether)

ORD-Eintrag

ord-a3cc92de7d0e45d5b4c1be93fb070ca5

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08367706B2