Diisopropylamine → HCID 14043104, compound

Participants

Reaction Conditions

Reaction Steps

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]

Provenance & Evidence