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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2363621Generated: October 31, 2026

(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → (2S,3aS,7aS)-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}octahydro-1H-indole-2-carboxamide

https://huagongshe.com/reaction/2363621

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66590059—
Reactant(3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66590965—
ReactantN-Boc-N-methyl-3-tert-butyl-L-alanineHCID 86641984—
Product(2S,3aS,7aS)-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}octahydro-1H-indole-2-carboxamideHCID 54672874—

Reaction Steps

The title compound was prepared by substituting (2S,3aS,7aS)-1-(tert-butoxycarbonyl)octahydro-1H-indole-2-carboxylic acid for (S)-2-(tert-butoxycarbonyl(methyl)amino)-4,4-dimethylpentanoic acid and (3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine from Example 262 Step B for (3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 587: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.66-8.59 (m, 1H), 8.32 (d, J=7.9, 1H), 7.67 (dd, J=8.9, 2.5, 1H), 6.36 (d, J=8.9, 1H), 4.38-4.29 (m, 1H), 3.94 (dd, J=10.6, 4.7, 1H), 3.72 (d, J=8.1, 1H), 3.58 (t, J=9.5, 2H), 3.33 (d, J=6.7, 1H), 3.23 (dd, J=9.4, 4.7, 1H), 3.18-2.94 (m, 1H), 2.80-2.68 (m, 1H), 2.66-2.57 (m, 1H), 2.27 (ddd, J=12.8, 10.6, 7.0, 1H), 2.15-2.05 (m, 1H), 1.96 (dddd, J=18.4, 16.6, 8.6, 4.9, 2H), 1.88-1.79 (m, 1H), 1.70-1.35 (m, 8H), 1.35-1.27 (m, 1H), 1.16 (tt, J=15.5, 6.5, 1H); MS (ESI+) m/z 423 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08691865B2
Source datasetuspto-grants-2014_04
ORD IDord-e933a86156874bc59b71d911ef5be424
Source noteuspto-grants-2014_04