Nitrogen → HCID 14098149, compound

Participants

Reaction Conditions

Reaction Steps

60 mmol of diisopropylamine in 100 ml of analytical grade tetrahydrofuran are initially taken. 50 mmol of butyllithium are added at a temperature of 0°C., under a stream of N2. Thereafter, the mixture is cooled to -78° C. and a solution of 50 mmol of isopropyl 4-(2-chlorophenyl)-1-ethyl-2-methyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine3-carboxylate (dissolved in THF) is added dropwise. The mixture is stirred for 15 minutes at -78° C., and this solution is pumped, with the aid of nitrogen, into a solution of 50 mmol of Br2 and 50 ml of THF, and immediately thereafter 50 mmol of cyclohexene are added and the mixture is allowed to warm up to room temperature and is evaporated down, the residue is dissolved in DMSO, and H2O is added until the mixture starts to become cloudy. The mixture is left to stand for 12 hours, and the product is precipitated with H2O, filtered off under suction and separated with 9:1 CHCl3 /MeOH over silica gel.

Provenance & Evidence