Sodium → HCID 11183440, compound

A solution of quinolinecarboxylate (obtained in Stage 83f; 1.8 g; 6.7 mmol) in dichloromethane (40 ml) under argon is treated dropwise with diisobutylaluminium hydride (1M in dichloromethane; 20 ml; 20 mmol) at ambient temperature maintained at 10° C. by an ice-cooled water bath. The reaction mixture is agitated for 1 hour at ambient temperature, then poured onto a solution of sodium and potassium tartrate at 20% (200 ml). The resulting mixture is agitated vigorously for 1 hour, then filtered on celite. The filtrate is extracted with dichloromethane (2×100 ml). The combined extracts are washed with water and with a saturated solution of sodium chloride, then dried over magnesium sulphate and concentrated. Purification of the residue by chromatography at medium pressure (SiO2, CH2Cl2/MeOH, 98/2) yields 450 mg of a white solid (m.p.: 176° C.).

1. temperaturecooled water bath
2. stirringThe resulting mixture is agitated vigorously for 1 hour
3. filtrationfiltered on celite
4. extractionThe filtrate is extracted with dichloromethane (2×100 ml)
5. washThe combined extracts are washed with water and with a saturated solution of sodium chloride
6. dry with materialdried over magnesium sulphate
7. concentrationconcentrated
8. customPurification of the residue by chromatography at medium pressure (SiO2, CH2Cl2/MeOH, 98/2)

ORD record

ord-24218f968e764ae8bb7e488db62a757e

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07135478B2