Pyridine → HCID 86638961, compound

Participants

Reaction Steps

A solution of N-bromosuccinimide (2.129 g, 11.96 mmol) in DCM (10 ml) was treated with triphenylphosphine (2.93 g, 11.17 mmol) in DCM (10 ml), followed by pyridine (0.387 ml, 4.79 mmol) and tert-butyl 5-hydroxy-N-{[2-(trimethylsilyl)ethoxy]carbonyl}-L-norvalinate (1.33 g, 3.99 mmol) in DCM (5 ml). The resulting black mixture was stirred at room temp for 24 h. The mixture was pre-absorbed onto SiO2 and purified by chromatography (silica gel, 0-5-10-20% Et2O/isohexane) to afford tert-Butyl 5-bromo-N-{[2-(trimethylsilyl)ethoxy]carbonyl}-L-norvalinate Intermediate 5 (1.1 g) as a colourless oil.

Provenance & Evidence