(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → N2-methyl-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}-L-norleucinamide

HRID 2363620Notes

Reaction equation

HRID 2363620 reaction equation
C(O[C:6]([N:8](C)[C@@H:9]([CH2:13][C:14]([CH3:17])([CH3:16])C)[C:10](O)=O)=[O:7])(C)(C)C.[F:19][C:20]([F:37])([F:36])[C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:31][C@@H]3[C@@H](N)CC[C@@H]3C2)=[N:25][CH:26]=1.FC(F)(F)[C:40]1N=[C:44]([N:46]2C[C@@H]3[C@@H](N)CC[C@@H]3[CH2:47]2)[CH:43]=[CH:42][CH:41]=1>>[CH3:47][NH:46][C@H:44]([C:6]([NH:8][C@@H:9]1[C@@H:13]2[C@@H:14]([CH2:16][N:27]([C:24]3[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:36])[F:37])=[CH:26][N:25]=3)[CH2:31]2)[CH2:17][CH2:10]1)=[O:7])[CH2:43][CH2:42][CH2:41][CH3:40]

Participants

4

Reactant 3

HCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66590965(3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 86641984N-Boc-N-methyl-3-tert-butyl-L-alanine

Product 1

HCID 66996871N2-methyl-N-{(3aR,4S,6aS)-2-[5-(trifluoromethyl)pyridin-2-yl]octahydrocyclopenta[c]pyrrol-4-yl}-L-norleucinamide

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-norleucine 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 8.64-8.59 (m, 1H), 8.27 (d, J=7.5, 1H), 7.68 (dd, J=8.9, 2.5, 1H), 6.39 (d, J=8.9, 1H), 4.47-4.39 (m, 1H), 3.83 (d, J=10.5, 1H), 3.71-3.64 (m, 1H), 3.62-3.54 (m, 1H), 3.33 (d, J=8.5, 1H), 3.19 (dd, J=6.9, 6.2, 1H), 2.81-2.70 (m, 2H), 2.44 (s, 3H), 2.21-2.13 (m, 1H), 2.16-2.03 (m, 1H), 2.01-1.90 (m, 1H), 1.86 (ddt, J=13.3, 10.3, 5.9, 1H), 1.77-1.64 (m, 2H), 1.55-1.37 (m, 3H), 1.32-1.20 (m, 2H), 0.83 (t, J=7.3, 3H); MS (ESI+) m/z 399 (M+H)+.

Sources & evidence

ORD record
ord-07d72c5ee302449f88cecaa46cf2abb3
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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