Stannous Chloride → 2-(4-Aminophenyl)-6-methoxy-1-[4-(phenylmethoxy)benzyl]-1,2,3,4-tetrahydroisoquinoline

Temperature

60 °C

A suspension of 6-methoxy-2-(4-nitrophenyl)-1-[4-(phenylmethoxy)benzyl]-1,2,3,4-tetrahydroisoquinoline (0.70 g, 1.46 mmol) and SnCl2*H2O (1.35 g, 6.0 mmol) in 20 mL of THF/HOAc (1:1) and 3 mL of water was heated at 60° C. for 3 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was quenched by the addition of saturated aqueous NaHCO3 (50 mL). The aqueous layer was extracted with EtOAc (3×50 mL) and the combined organic layer was dried over MgSO4 then concentrated. The crude product was purified by flash chromatography to provide the title compound (0.63 g, 95% yield). ES-MS, (m/z) 451 [M+H]+.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. customthe resulting residue was quenched by the addition of saturated aqueous NaHCO3 (50 mL)
3. extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
4. dry with materialthe combined organic layer was dried over MgSO4
5. concentrationthen concentrated
6. customThe crude product was purified by flash chromatography

ORD record

ord-2b0205e926754319a05a05c28f3dd87e

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07435729B2