Water → HCID 24851751, compound

Participants

Reaction Steps

To a stirred solution of the compound obtained from example 29 (0.2 g, 0.51 mmol) in a 1:2:4 mixture of water, THF, and ethanol (7 mL) respectively was sequentially added solid NH4Cl (0.1 g, 1.87 mmol) and Fe powder (0.1 g, 1.78 mmol). The reaction mixture was heated to reflux for 2 h. After cooling the reaction mixture to room temperature, it was filtered through a small pad of celite and washed the bed with EtOAc. The filtrate was evaporated under reduced pressure and the residue was diluted with water and extracted with EtOAc. The combined organic layer was washed with water, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to obtain (2S)-1-{N-[2-(4-aminophenyl)hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile as off-white solid (0.09 g) in 50% yield. m/z (M+1) 365; 1H NMR (CDCl3) 300 MHz δ 7.05 (d, J=8.5 Hz, 2H), 6.63 (d, J=8.5 Hz, 2H), 4.90-4.75 (m, 1H), 3.80-3.40 (m, 4H), 2.45-1.70 (m, 15H), 1.65-1.57 (m, 1H).

Provenance & Evidence