Lithium Hexamethyldisilazide → HCID 67612488, compound

Participants

Reaction Steps

To a solution of the piperazinone from Step I (98.0 mg, 0.316 mmol) in 1.5 mL of THF at -78 ° C. was added dropwise 1M lithium hexamethyldisilazide solution (0.332 mL, 0.332 mmol). After 20 minutes. a solution of the aldehyde from Step E (76 mg, 0.360 mmol) in 0.5 mL of THF was added. After 30 min, the reaction was quenched with sat aq. NH4Cl soln., poured into EtOAc, and washed with sat. aq. NaHCO3 soln., and brine. The solution was dried (Na2SO4), filtered, and concentrated in vacuo to provide the crude product. The product was purified by flash chromatography on silica gel (3-6% MeOH/CH2Cl2) to provide 60 mg of the titled product as a 9:1 mixture of diastereomers.

Provenance & Evidence