Diisopropylamine → HCID 14043104, compound

Temperature

-78 °C

To a solution of diisopropylamine (342 μL, 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 μL, 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 me, 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 NH4C1, 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 (400MHz, CDCl3) δ1.41 (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). [Compound 44 is hereinafter also referred to as COMPOUND "G" or 1201381]

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 NH4C1
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-79b70e3e3c1e4015adcc721b5c65d631

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05677336