Sodium borohydride → 1-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Temperature

0 °C

To a solution of 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (4.693 g, 17 mmol) (example 1b) in MeOH (24 mL) was added sodium borohydride (1.94 g, 51.1 mmol) slowly at 0° C. After addition, the mixture was stirred at 0° C. for 15 min and at RT for 2 h. The solvent was then removed and H2O (20 mL) was added to the residue. Then, a saturated NaHCO3 solution (150 mL) was added slowly and the mixture was extracted with EtOAc (2×200 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was mixed with silica gel (4:1; residue:silica gel). The solid mixture was purified by silica gel flash column chromatography using ISCO instrument (solid loading, 20%-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 278 (M+H).

1. additionAfter addition
2. customThe solvent was then removed
3. additionH2O (20 mL) was added to the residue
4. additionThen, a saturated NaHCO3 solution (150 mL) was added slowly
5. extractionthe mixture was extracted with EtOAc (2×200 mL)
6. dry with materialThe combined organic extracts were dried over MgSO4
7. concentrationconcentrated
8. additionThe residue was mixed with silica gel (4:1; residue:silica gel)
9. customThe solid mixture was purified by silica gel flash column chromatography

ORD record

ord-c760b799ee4b4f8d893057c45863fc2e

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476297B2