Lithium Hexamethyldisilazide → HCID 67151379, compound

Participants

Reaction Conditions

Reaction Steps

1.49 g (4 mmol) of di-tert-Butyl (2S)-2-[(tert-butoxycarbonyl)amino]hexanedioate 7a were dissolved in 50 mL of THF and cooled to −70° C. 8.8 mL (8.8 mmol) of a 1M solution of lithium bis(trimethylsilyl)amide in THF were added dropwise over a period of two hours at this temperature and the mixture was stirred at −70° C. for another 2 hours. 0.985 g (4.6 mmol) of 4-Cyano-3-fluorobenzyl bromide were then added dropwise, and after 2 h at this temperature, the cooling bath was removed and 20 mL of 2N aqueous hydrochloric acid and 100 mL of dichloromethane added. The organic phase was separated off, washed with water until neutral, dried over sodium sulphate and filtered, and the filtrate was concentrated. The crude product obtained in this manner was chromatographed on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated (150 mg) MS (ESIpos): m/z=507 [M+H]+

Provenance & Evidence