tert-Butyl (2R)-2-ethenylpyrrolidine-1-carboxylate → (S)-N-tert-Butoxycarbonyl-2-ethylpyrrolidine

Participants

Reaction Steps

Tert-butyl-(2R)-2-vinylpyrrolidine-1-carboxylate (0.21 g, 1.07 mmol) was dissolved in methanol (10 mL) with palladium on carbon, 10% catalyst (0.046 g, 20% by wt.) and subjected to a hydrogen atmosphere via balloon. The reaction was run overnight and filtered through Celite and concentrated in vacuo to yield tert-butyl (2S)-2-ethylpyrrolidine-1-carboxylate (0.18 g, HPLC RT=3.00 min.). LC-MS m/z (minus t-butyl+CH3CN+1)=185. 1H NMR (CD3OD, 400 Mhz) 3.67-3.63 ppm (m, 1H), 3.36-3.30 (m, 2H), 1.92-1.71 (m, 4H), 1.45 (s, 9H), 1.43-1.29 (m, 2H), 0.90-0.85 (t, 3H).

Provenance & Evidence