Diethyl Ether → HCID 11545724, compound

Participants

Reaction Steps

To a suspension of CuCN (22.5 mg, 0.25 mmol) in dry THF (2 ML) at −78° C., under nitrogen atmosphere, was added a solution of MeLi in Et2O (1.4 M, 0.37 mL, 0.5 mmol). The mixture was stirred for 30 min and treated drop wise with a solution of 7a-(4-cyanobenzyl)-6-(3,5-dichlorophenyl)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl trifluoromethanesulfonate 26 (50 mg, 0.09 mmol) in THF (1 mL). The reaction was stirred for 2 h at −78° C. and 20 min. at −20° C. The reaction was treated with 10% aqueous NH4OH (10 ml), stirred at rt. for 10 min. and extracted with Et2O (4×10 mL). The extracts were combined sat. NaCl solution (10 ml), dried (MgSO4) and solvent removed. The resulting oil was purified using preparative HPLC to give 4-{[6-(3,5-Dichlorophenyl)-7-methyl-5-oxo-2,3-dihydro-1H-pyrrolizin-7a(5H)-yl]methyl}benzonitrile IX (5 mg, 14%), LCMS (m/z) 397/399 (M++H), HPLC Retention Time/Condition 1: 1.86 min.

Provenance & Evidence