2-Bromoethanol → (R)-2-(2-methylpyrrolidin-1-yl)ethanol

A mixture of (R)-2-methylpyrrolidine hydrochloride (4 g, 0.03 mol), 2-bromoethanol (3.7 g, 0.029 mmol) and K2CO3 (8.28 g, 0.0618 mol) in acetonitrile (50 mL) was stirred at room temperature overnight. The mixture was filtered, and the filter cake was washed with ethyl acetate (100 mL). The combined filtrate was concentrated and the residue was purified on a silica gel column (MeOH/DCM=1/50) to give (R)-2-(2-methylpyrrolidin-1-yl)ethanol (0.9 g) as a colorless oil. 1H NMR (CDCl3): δ 3.63 (m, 2H), 3.14 (m, 1H), 2.95 (m, 1H), 2.44 (m, 1H), 2.24 (dt, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.68 (m, 2H), 1.38 (m, 1H), 1.07 (d, 3H); LCMS: 130 (M+H)+.

1. filtrationThe mixture was filtered
2. washthe filter cake was washed with ethyl acetate (100 mL)
3. concentrationThe combined filtrate was concentrated
4. customthe residue was purified on a silica gel column (MeOH/DCM=1/50)

ORD-Eintrag

ord-ef3f4a0e23b040a5b343cdbe79b2daa7

Quelldatensatz

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09078871B2