Ammonium Chloride → HCID 69330958, compound

Participants

Reaction Conditions

Reaction Steps

3.50 g (9.15 mmol) of the compound from example 12a were dissolved in 50 ml of dry THF and cooled to 0° C. 1.67 g (9.96 mmol) of lithium bis(trimethylsilyl)amide as 20% strength solution in THF were added dropwise to this solution while stirring. The resulting mixture was stirred at 0° C. for 30 min and then 0.86 g (10.07 mol) of methyl cyanoformate was added. The reaction mixture was warmed to RT and stirred for a further 2 h, then poured into 400 ml of saturated aqueous NH4Cl solution and extracted twice with EA. The combined organic phases were washed with water, dried over Na2SO4, filtered and concentrated. Chromatography of the residue on silica gel afforded 1.92 g of the title compound. Repeat chromatography of the resulting mixed fraction afforded a further 40 mg of the desired compound.

Provenance & Evidence