Methyl (S)-3-(5-aminopyridin-2-yl)-2-((tert-butoxycarbonyl)amino)propanoate → tert-butyl(2S)-6-amino-3-oxooctahydroindolizin-2-ylcarbamate

Participants

Reaction Steps

A solution of (S)-methyl 3-(5-aminopyridin-2-yl)-2-(tert-butoxycarbonylamino)propanoate (0.965 g, 3.27 mmol) 127.1 (prepared as described in WO2002068393) in glacial AcOH (40 mL) was treated with 5% Rh/C (0.67 g) and stirred at room temperature under a 60 psi H2 atmosphere for 25 hr. The catalyst was removed by filtration through a celite pad, rinsing with MeOH. The filtrate was concentrated to dryness and azeotroped from toluene (2×). The residue was dissolved in MeOH (50 mL) and treated with polymer-supported carbonate resin (2.5 g, 3.5 mmole/g) and stirred at room temperature for 24 hr. The resin was removed by filtration and the filtrate concentrated in vacuo to afford of tert-butyl (2S)-6-amino-3-oxooctahydroindolizin-2-ylcarbamate (0.913 g) 127.2 as a clear viscous oil that was used without further purification. LCMS (ESI) m/z: 270.2 [M+H]+.

Provenance & Evidence