L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → N-[(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-3-methylbutanamide

Participants

Reaction Steps

The title compound was prepared by substituting 3-methylbutanoic acid for N-(tert-butoxycarbonyl)-L-leucine and (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Step E of Example 16 for (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 221: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.30-8.17 (m, 1H), 7.43 (dd, J=11.2, 4.2, 2H), 7.37 (t, J=7.5, 2H), 7.27 (t, J=7.3, 1H), 4.49-4.39 (m, 1H), 3.60 (d, J=13.1, 1H), 3.45 (d, J=13.1, 1H), 2.89-2.78 (m, 1H), 2.55-2.49 (m, 2H), 2.45 (dd, J=10.4, 5.3, 1H), 2.36-2.24 (m, 3H), 2.21 (d, J=7.1, 2H), 2.17-2.08 (m, 1H), 1.90-1.79 (m, 1H), 1.62 (ddd, J=15.1, 12.3, 7.2, 1H), 1.40 (dtd, J=9.2, 8.2, 6.1, 1H), 0.95 (d, J=6.6, 6H); MS (ESI+) m/z 301 (M+H)+.

Provenance & Evidence