Hydrochloric Acid → 2-benzyl-6-hydroxymethyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

To a solution of 2-benzyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic acid 3-methyl ester (300 mg) in THF (3 ml) was added dropwise a solution (1M, 1.5 ml) of borane complex in THF under ice-cooling, and the mixture was allowed to warm to room temperature and stirred for 4 hrs. To the reaction mixture was further added dropwise a solution (1M, 3 ml) of borane complex in THF at room temperature, and the mixture was stirred for 1 hr. To the reaction mixture were added water and 10% hydrochloric acid under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate-hexane to give the title compound (280 mg).

1. temperaturecooling
2. stirringthe mixture was stirred for 1 hr
3. temperaturecooling
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with water, saturated aqueous sodium hydrogen carbonate, water and saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe obtained residue was crystallized from ethyl acetate-hexane

ORD 기록

ord-32bfcfe8c0274daa836b7f9c24aa9453

출처 데이터셋

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07402595B2