Sodium Carbonate → Methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

온도

80 °C

A solution of methyl 2-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (200.0 mg, 0.600 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (188.8 mg, 0.6107 mmol) in DME (5.15 mL) was treated with Na2CO3 (2.00 M in water, 0.83 mL, 1.66 mmol). The mixture was degassed and Pd(Ph3P)4 (13 mg, 0.011 mmol) was added. The reaction mixture was heated under argon at 80° C. overnight. The mixture was then cooled to room temperature and diluted with water. The aqueous phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (SiO2, 10-50% EtOAc in hexanes) to give methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (228 mg, 89%). LC-MS: (FA) ES+ 263.

1. customThe mixture was degassed
2. temperatureThe mixture was then cooled to room temperature
3. extractionThe aqueous phase was extracted twice with EtOAc
4. washThe combined organic phases were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by column chromatography (SiO2, 10-50% EtOAc in hexanes)

ORD 기록

ord-f5029909870845f9ab7a80b7ea9c6466

출처 데이터셋

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08778931B2