Boron trifluoride etherate → HCID 9943474, compound

Participants

Reaction Steps

To a solution of the crude 4-(4-methoxybenzo[b]thiophen-2-yl)-2-methyl-3,4,5,6-tetrahydropyridine (2.19 g, 8.44 mmol) in THF (38 mL) cooled to −78° C. in a dry ice/acetone bath, was added dropwise BF3.Et2O (48%) (3.34 mL, 12.6 mmol) via a syringe. After stirring ten minutes, the solution was treated with 24.1 mL (33.77 mmol) of 1.4 M MeLi. The mixture was stirred for 16 h, then quenched with 100 mL of saturated aqueous NH4Cl and 50 mL of H2O. The mixture was then extracted with CH2Cl2 (3×100 mL). The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography [2.5 to 7% (2.0 M NH3 in MeOH)/CH2Cl2] to give the title compound as an orange oil (0.713 g, 30%). IR (KBr) 2936, 1571, 1471, 1259, 1049 cm1. Ion Spray MS 276.2 (M+H)+. [α]D=0 (c 0.578, MeOH). C16H21NOS.0.1H2O.0.1 CH2Cl2

Provenance & Evidence