Potassium Carbonate → (2S,4R)-N-(4-Chloro-phenyl)-N-{1-[4-(4-hydroxy-4-methyl-pentyloxy)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide

Temperature

80 °C

(2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (0.1 g, 0.23 mmol) was dissolved in DMF (5 mL) at room temperature. K2CO3 (0.317 g, 2.3 mmol) was added. 5-Bromo-2-methyl-pentan-2-ol (0.092 g, 0.51 mmol) was added and the reaction was allowed to heat to 80° C. overnight. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated down. The crude residue was purified by silica gel chromatography (70% EtOAc/30% Hexane) to afford the product (0.097 g, 79%).

1. concentrationThe reaction mixture was concentrated in vacuo
2. customThe residue was partitioned between ethyl acetate and water
3. extractionextracted three times with ethyl acetate
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated down
7. customThe crude residue was purified by silica gel chromatography (70% EtOAc/30% Hexane)

ORD record

ord-8f7997eefabb47a8868bf467e90a5a97

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504508B2