Boron trifluoride etherate → HCID 53847367, compound

Participants

Reaction Steps

N-Benzyloxy-1-(1-methyl-5-phenylpyrrol-2-yl)ethylamine. t-Butyl lithium (4.1 ml, 1.7M in hexanes) was added to a solution of the pyrrole prepared as in step a, above (1.0 g, 6.4 mmole) in THF (25 mL) at -78° C. After stirring for 30 minutes, boron trifluoride etherate (0.99 g, 7.0 mmole) was added followed by O-benzyl acetaldehyde oxime (1.0 g, 7.0 mmole). The mixture was stirred for 15 min, saturated NH4Cl solution was added, and the mixture was allowed to warm to room temperature. The aqueous phase was washed twice with brine, dried over MgSO4 and concentrated. The residue was chromatographed on 100 g of silica gel eluting with 20% ether in hexanes to give 0.34 g of the desired product.

Provenance & Evidence