(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → HCID 66997207, compound

HRID 2363657Notes

Reaction equation

C(OC([N:8]([CH3:18])[C@@H:9]([CH2:13][C:14]([CH3:17])([CH3:16])C)[C:10]([OH:12])=O)=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>>[CH3:18][NH:8][C@@H: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:37])([F:19])[F:36])=[CH:26][CH:25]=3)[CH2:31]2)[CH2:34][CH2:33]1)=[O:12])[CH2:13][CH:14]([CH3:16])[CH3:17]

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 66997207HCID 66997207, compound

Procedure

The title compound was prepared by substituting (S)-N-(tert-butoxycarbonyl)-N-methyl-D-leucine 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 (500 MHz, pyridine-d5) δ ppm 8.36 (d, J=7.4, 1H), 7.57 (d, J=8.6, 2H), 6.63 (d, J=8.7, 2H), 4.46-4.37 (m, 1H), 3.56 (dd, J=10.1, 3.0, 1H), 3.38 (dd, J=10.0, 7.6, 1H), 3.30-3.19 (m, 2H), 3.02 (dd, J=9.9, 3.7, 1H), 2.73 (ddd, J=13.1, 8.2, 6.7, 2H), 2.46 (s, 3H), 2.18-2.09 (m, 1H), 2.11-2.01 (m, 1H), 2.00-1.87 (m, 2H), 1.80-1.58 (m, 3H), 1.39 (dtd, J=13.2, 8.0, 5.2, 1H), 0.94 (d, J=6.6, 3H), 0.88 (d, J=6.6, 3H); MS (ESI+) m/z 398 (M+H)+.

Sources & evidence

ORD record: ord-06a3beed6f1849c2b146096d588acff6
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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