Cyclohexylisopropylamine → HCID 23370054, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclohexylisopropylamine (1.42 ml) in dry THF (3 ml) at -76° C. under argon was added a 2.5M solution of n-butyllithium in hexane (3.5 ml). The resultant solution was stirred at -76° C. for 15 minutes before a solution of the product from step (b) (1 g) in dry THF (7 ml) was added dropwise. On completion of the addition, the reaction mixture was allowed to warm to 0° C. and stirred at that temperature for 15 minutes before a solution of 4-nitrobenzyl bromide (940 mg) in dry THF (3 ml) was added, followed by 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.5 ml). The resultant mixture was stirred at ambient temperature for 16 hours and then heated to reflux for 5 hours. The reaction mixture was evaporated to dryness and saturated ammonium chloride solution was added to the residue. The resultant mixture was extracted thoroughly with ethyl acetate and the combined extracts were washed with brine, dried (MgSO4) and evaporated to give a residue which was purified by flash chromatography on silica by elution with 20% ethyl acetate/hexane to give t-butyl 2-(2-ethoxyethyl)-3-(4-nitrophenyl)propionate (940 mg) as a pale yellow oil: NMR Spectrum (CDCl3) 1.19 (3H, t), 1.33 (9H, s), 1.76 (1H, m), 1.94 (1H, m), 2.78 (1H, m), 2.91 (2H, m), 3.44 (4H, m), 7.35 (2H, d), 8.13 (2H, d); Mass Spectrum m/Z 324 (M+H)+.

Provenance & Evidence