(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → HCID 66997462, compound

HRID 2363625Notes

Reaction equation

HRID 2363625 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:22]=[C:23]([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:24]=[CH:25][CH:26]=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:23]3[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:37])([F:19])[F:36])[CH:22]=3)[CH2:31]2)[CH2:34][CH2:33]1)=[O:12])[CH2:13][CH:14]([CH3:16])[CH3:17]

Participants

4

Reactant 3

HCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66996984HCID 66996984, compoundHCID 86641984N-Boc-N-methyl-3-tert-butyl-L-alanine

Product 1

HCID 66997462HCID 66997462, compound

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-leucine for (S)-2-(tert-butoxycarbonyl(methyl)amino)-4,4-dimethylpentanoic acid and (3aR,4S,6aS)-2-[3-(trifluoromethyl)phenyl]octahydrocyclopenta[c]pyrrol-4-amine from Example 605 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 8.34 (d, J=7.4, 1H), 7.34 (t, J=7.9, 1H), 7.06 (d, J=7.6, 1H), 6.94 (s, 1H), 6.78 (dd, J=8.3, 2.2, 1H), 4.46-4.38 (m, 1H), 3.55 (dd, J=9.9, 2.8, 1H), 3.37-3.32 (m, 1H), 3.27 (dd, J=8.3, 5.8, 1H), 3.17 (dd, J=9.5, 7.9, 1H), 3.01 (dd, J=9.7, 3.3, 1H), 2.79-2.70 (m, 2H), 2.46 (s, 3H), 0.2-1.86 (br s, 1H), 2.13 (dt, J=12.5, 6.7, 1H), 2.01-1.87 (m, 2H), 1.79-1.65 (m, 2H), 1.65-1.57 (m, 1H), 1.46-1.38 (m, 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-81ad4c7172734d0db2ab1efdaf83804f
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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