Boron trifluoride → α-Cyclopropyl-6-methoxy-N-(phenylmethoxy)-2-pyridinemethanamine

Participants

Reaction Conditions

Reaction Steps

8.8 ml (22 mmol) of n-BuLi (2.5 M in toluene) were added to 3.76 g (20 mmol) of 2-bromo-6-methoxypyridine in 20 ml of THF at −78° C. After 30 min, this dark red solution was added to a solution of 1.4 g (8 mmol) of cyclopropanecarbaldehyde O-benzyloxime (see a) and 2.52 ml (20 mmol) of BF3 etherate in 40 ml of toluene which had been stirred at −78° C. for 15 min. The mixture was stirred at −78° C. for 4 h, slowly warmed to RT and, after addition of water, made alkaline with saturated Na2CO3 solution.

Provenance & Evidence