(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → HCID 66997212, compound

HRID 2363652Notes

Reaction equation

C(O[C:6]([N:8](C)[C@@H:9](CC(C)(C)C)[C:10](O)=[O:11])=O)(C)(C)C.[F:19][C:20]([F:37])([F:36])[C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH2:35])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)=[CH:23][CH:22]=1.FC(F)(F)C1N=C(N2C[C@@H]3[C@@H](N)CC[C@@H]3C2)C=CC=1>>[CH3:6][NH:8][CH2:9][C:10]([NH:35][C@@H:32]1[C@@H:30]2[C@@H:29]([CH2:28][N:27]([C:24]3[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:36])[F:37])=[CH:26][CH:25]=3)[CH2:31]2)[CH2:34][CH2:33]1)=[O:11]

Participants

Reactant 3

HCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine

HCID 66996860HCID 66996860, compound

HCID 86641984N-Boc-N-methyl-3-tert-butyl-L-alanine

Product 1

HCID 66997212HCID 66997212, compound

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-glycine for (S)-2-(tert-butoxycarbonyl(methyl)amino)-4,4-dimethylpentanoic acid and (3aR,4S,6aS)-2-[4-(trifluoromethyl)phenyl]octahydrocyclopenta[c]pyrrol-4-amine from Example 607 for (3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 587: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.11 (d, J=7.3, 1H), 7.57 (d, J=8.6, 2H), 6.61 (d, J=8.7, 2H), 4.42-4.27 (m, 1H), 3.51 (dd, J=10.2, 3.3, 1H), 3.42 (d, J=1.0, 2H), 3.32 (dd, J=10.1, 7.8, 1H), 3.21 (dd, J=9.8, 8.1, 1H), 3.00 (dd, J=9.9, 4.1, 1H), 2.74-2.60 (m, 2H), 2.45-2.35 (bs, 1H), 2.40 (s, 3H), 2.08 (ddd, J=19.2, 7.0, 5.1, 1H), 1.92 (dtd, J=12.9, 7.9, 5.0, 1H), 1.62 (ddd, J=16.0, 12.6, 7.9, 1H), 1.42-1.27 (m, 1H); MS (ESI+) m/z 342 (M+H)+.

Sources & evidence

ORD record: ord-7f903a8b36c04f65bca1c09c19f71bbf
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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