2-Chlorobenzylamine → N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide

Temperatur

80 °C

To a solution of methyl 3-hydroxy-2,2-dimethylpropanoate (1.0 g, 7.57 mmol) and 2-chlorobenzylamine (1.09 mL, 9.08 mmol, 1.2 equiv.) in toluene (10 mL) was added trimethylaluminum (2M in hexanes, 5.6 mL, 11.4 mmol, 1.5 equiv.). The reaction mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated. The resulting residue was dissolved in EtOAc (100 mL). The organic layer was washed with saturated NaHCO3, dried over Na2SO4, and concentrated. The resulting residue was purified on silica gel column using a mixture of hexanes and ethyl acetate to give N-(2-chlorobenzyl)-3-hydroxy-2,2-dimethylpropanamide (1.55 g, 84%). LRMS (M+H+) m/z 242.1.

1. concentrationThe reaction mixture was concentrated
2. dissolutionThe resulting residue was dissolved in EtOAc (100 mL)
3. washThe organic layer was washed with saturated NaHCO3
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe resulting residue was purified on silica gel column
7. additiona mixture of hexanes and ethyl acetate

ORD-Eintrag

ord-74d8738b1782456c9ad0e5214729b31e

Quelldatensatz

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08071625B2