phenylmethyl (2S)-2-(aminocarbonyl)-3,3-dimethyl-1-pyrrolidinecarboxylate → (S)-3,3-dimethylpyrrolidine-2-carboxamide

Participants

Reaction Steps

In a 200 ml flask was dissolved phenylmethyl (2S)-2-(aminocarbonyl)-3,3-dimethyl-1-pyrrolidinecarboxylate (0.0192 mol, 5.3 g) in 80 ml methanol at 20° C. 10% Pd/C (Degussa type, 0.53 g) was added and the mixture was stirred for 5 hr under atmospheric H2. The catalyst was filtered and the reaction was concentrated yielding 2.8 g (quantitative) of 3,3-dimethyl-L-prolinamide as a white solid. LCMS (ESI+)=143 m/z (MH+). 1H NMR (400 MHz, CDCl3)— rotomers δ 7.20 (bs, 1H), 6.20 (bs, 1H), 3.32 (s, 1H), 3.05-3.01 (m, 2H), 2.50 (bs, 1H), 1.67-1.62 (m, 2H), 1.23 (s, 3H), 0.97 (s, 3H). [α]D +1.2° (c=0.5, methanol)

Provenance & Evidence