Hydrochloric Acid → (R)-Pyrrolidin-2-yl((R)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-yl)methanone

To a stirred mixture of (R)-1-(tert-butoxy-carbonyl)pyrrolidine-2-carboxylic acid (0.078 g, 0.36 mmol), (R)-1-(4-(trifluoro-methyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.100 g, 0.36 mmol) and DIEA (0.047 g, 0.36 mmol) in DMF (2 mL) was added HATU (0.14 g, 0.36 mmol). The reaction mixture was continued to stir overnight at RT, hydrolyzed with H2O, extracted with DCM (3×), dried over Na2SO4, concentrated and purified by ISCO (20% EtOAc/hexanes) to give the white solid which was dissolved in p-dioxane (2 mL) and added 1 mL of 4M HCl in p-dioxane. The mixture was continued to stir at RT overnight, concentrated, taken up in H2O, and neutralized by saturated aqueous NaHCO3, and filtered the light yellow solid which was dried by air. MS (ESI, positive ion) m/z: 375 (M+1).

1. extractionextracted with DCM (3×)
2. dry with materialdried over Na2SO4
3. concentrationconcentrated
4. custompurified by ISCO (20% EtOAc/hexanes)
5. customto give the white solid which
6. concentrationconcentrated
7. filtrationfiltered the light yellow solid which
8. customwas dried by air

ORD record

ord-9a93e900122a4fc9b1bab144aa9bc64f

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476297B2