Borane;tetrahydrofuran → 4-[(Indolizin-3-yl)methyl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

To 4-(indolizine-3-carbonyl)-benzonitrile (24 g, 100 mmol) CH3CN (600 ml) solution containing MeOH (9 ml) was added BH3-THF (1M, 480 ml). The resulting mixture was stirred at 50° C. for 1 hr. The reaction was quenched with water (200 ml), and extracted with EtOAc (700 ml), and washed with water (300 ml×3). The organic layer was evaporated under reduced pressure, and the residue was dissolved in ether (or EtOAc) (400 ml), diluted with hexanes (100 ml) and filtered with celite to give 4-indolizin-3-ylmethyl-benzonitrile (15.6 g, 92% purity by HPLC). This product was used directly for the next step. δ (ppm) 8.54 (m, 1H); 7.59 (m, 3H); 7.39 (m, 2H); 7.31 (m, 1H); 7.19 (m, 1H); 3.01 (t, J=6.9 Hz, 2H); 2.75 (t, J=6.9 Hz, 2H). ESMS calcd. (C16H12N2): 232.1. found: 233.1 (M+H)+.

Provenance & Evidence