Diisopropylamine → HCID 14043104, compound

Temperature

-78 °C

To a solution of diisopropylamine (342 mL, 2.45 mmol, 1.2 equiv) in 5 mL of anhydrous THF at 0° C. was added n-butyllithium (1.63 mL of a 1.6M solution in hexane), and the mixture was stirred at this temperature for 15 minutes before cooling to -78° C. Cyclohexanone (221 mL, 2.04 mmol, 1.0 equiv) in 2 mL of anhydrous THF was then added dropwise, stirred at -78° C. for 1 h followed by p-nitrobenzyl bromide (880 mg, 4.08 mmol, 2.00 equiv) in 2 mL of THF, added dropwise to the resulting enolate. The reaction mixture was stirred at room temperature for 17 h, and then quenched with aqueous saturated NH4Cl, and extracted with ether. The organic phase was dried over Na2SO4 and concentrated under diminished pressure to a solid residue that was purified by flash chromatography (silica gel, hexanes/ethyl acetate, 85:15), which afforded 300 mg (64%) of the desired ketone as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 1.41 (m, 1H), 1.66 (m, 2H), 1.88 (m, 1H), 2.08 (m, 2H), 2.33 (m, 1H), 2.45 (m, 1H), 2.57 (m, 1H, 2-H), 2.59 and 3.29 (d of ABq, 2H, benzylic-CH2), 7.34 (d, 2H, Ar--H), 8.12 ppm (d, 2H, Ar--H). [This compound is also referred to as Compound "F" or 120138]

1. stirringstirred at -78° C. for 1 h
2. stirringThe reaction mixture was stirred at room temperature for 17 h
3. customquenched with aqueous saturated NH4Cl
4. extractionextracted with ether
5. dry with materialThe organic phase was dried over Na2SO4
6. concentrationconcentrated under diminished pressure to a solid residue that
7. customwas purified by flash chromatography (silica gel, hexanes/ethyl acetate, 85:15), which

ORD record

ord-ff7c0b90930e462d9ef55cf4d7e50643

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05808139