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

温度

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レコード

ord-6816fca1f4a94d8fba23c0eb79d2db2c

出典データセット

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06593322B1