Triethylamine → HCID 54128708, compound

Participants

Reaction Steps

A solution of the compound of Example 19 (0.491 g, 1.3 mmol), hydroxylamine hydrochloride (0.092 g, 1.3 mmol), and triethylamine (0.18 mL, 1.3 mmol) in absolute EtOH (10 mL) was heated to reflux (86°-90° C.). After 5 hours, TLC [1:1 EtOAc/hexane (10 mL) and 5 drops of AcOH] showed that starting material was still present. Additional hydroxylamine hydrochloride (0.038 g, 0.5 eq) and triethylamine (0.09 mL) was added. After 40 minutes, the TLC showed no difference. The reaction was concentrated in vacuo to give a pale yellow oil (0.53 g). The oil was purified by column chromatography [50 g silica gel, 3% MeOH/CH2 Cl2 (500 mL) followed by 10% MeOH/CH2Cl2 (150 mL)] and the desired product was collected in 85% yield (0.42 g). NMR was consistent with proposed structure.

Provenance & Evidence