Nitrogen → HCID 67128531, compound

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a degassed solution of dicyclohexylamine (1.03 mL, 5.18 mmol) in toluene (30 mL) was treated 0° C. with n-BuLi (2.07 mL of a 2.5M solution in hexane, 5.18 mmol) and the reaction was stirred at 0° C. for 30 min. Acetic acid tert-butyl ester (0.59 mL, 4.40 mmol) was added dropwise and the reaction mixture was stirred at 0° C. for 50 min. To this solution was added a degassed suspension of 2-(3-bromo-phenyl)-2-methyl-[1,3]dioxolane (972 mg, 4.00 mmol) and {[P(t-Bu)3]PdBr}2 (25 mg, 0.03 mmol) and the reaction mixture was stirred at rt for 5 h. The reaction volume was reduced to half by rotary evaporation. The concentrated solution was washed with sat. aq. NH4Cl (30 mL). A large amount of precipitate formed between the aq. and org. layers. The org. layer was separated, and the aq. layer was washed with ether (5×20 mL). The combined org. layers were dried over MgSO4, filtered, and the solvent was removed under reduced. Purification of the residue by FC (9:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (9:1 hept-EA)=0.26. LC-MS-conditions 02: tR=1.05 min.

Provenance & Evidence