Acetyl chloride → HCID 18655452, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, a solution of the (4S)-3-(3-cyclopropyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone (6.01 g, 22.0 mmol, described in example 3) in anhydrous THF (10 mL) was added to a cold (-78°) stirred solution of lithium diisopropylamide (963 mg, 9.0 mmol) in anhydrous THF (10 mL). The mixture was stirred at -78° for 45 min and then transferred by cannula into a cold (-78°) solution of acetyl chloride (0.86 mL, 12 mmol) in anhydrous THF (5 mL). The resultant mixture was stirred for 15 min at -78° C., then quenched with a saturated aqueous solution of NH4Cl, allowed to warm to room temperature (20°-22°) and diluted with Et2O. The layers were separated and the aqueous phase was extracted with Et2O.

Provenance & Evidence