HCID 69893528, compound → HCID 69892414, compound

Participants

Reaction Steps

(S)-1-Benzyl-5-nitromethylene proline methyl ester (3.22 g, 11.6 mmol) was added to a suspension of 10% palladium on carbon (1.35 g) in methanol (75 mL) and the mixture was hydrogenated under 30 psi of hydrogen for 20 h. The catalyst was removed by filtration through a pad of celite and the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography, eluting with 5% methanol/methylene chloride, to yield the desired product (1.49 g, 60%). 1H NMR (300 MHz, CDCl3): δ 1.78 (m, 1 H), 2.08 (m, 1 H), 2.22 (m, 2 H), 2.99 (dd, 1 H, J=2.0, 11.3), 3.38 (m, 1 H), 3.49 (d, 1 H, J=6.1), 3.67 (dd, 1 H, J=3.9, 11.3), 3.78 (s, 2 H), 5.66 (s, 1 H), 7.33 (m, 5 H). MS ESI+: m/z 217 (M+H)+.

Provenance & Evidence