tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate → tert-Butyl 3-(5-((S)-1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (900 mg, 1.89 mmol) and Pd/C (100 mg) in EtOH (50 mL) was stirred at 27° C. for 3 hours under H2 (50 psi). The reaction mixture was subsequently filtered, and the filtrate was concentrated to dryness. The residue was purified by preparative HPLC to afford a mixture of the diastereomers of the title compound as a yellow oil (350 mg, 54%). 1H NMR (400 MHz, CDCl3) δ ppm 7.44 (d, J=6.4 Hz, 1H), 7.22 (d, J=3.2 Hz, 1H), 6.61 (d, J=3.2 Hz, 1H), 4.51 (q, J=6.4 Hz, 1H), 3.86-3.37 (m, 1H), 3.76 (s, 3H), 2.31-2.30 (m, 1H), 1.50 (s, 9H), 1.44 (d, J=6.4 Hz, 3H); ESI-MS m/z [M+H]+ calc'd for C19H28N4O2, 345. found 345.

Provenance & Evidence