(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → HCID 66997196, compound

HRID 2363665Notes

Reaction equation

HRID 2363665 reaction equation
C(OC([N:8]([CH3:18])[C@@H:9]([CH2:13][C:14](C)(C)C)[C:10]([OH:12])=O)=O)(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:30]3[C@@H:32]([NH2:35])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)=[N:25][CH:26]=1.[F:38]C(F)(F)C1N=C(N2C[C@@H]3[C@@H](N)CC[C@@H]3C2)C=CC=1>>[F:38][C@H:14]1[CH2:18][NH:8][C@H:9]([C:10]([NH:35][C@@H:32]2[C@@H:30]3[C@@H:29]([CH2:28][N:27]([C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:36])[F:37])=[CH:26][N:25]=4)[CH2:31]3)[CH2:34][CH2:33]2)=[O:12])[CH2:13]1

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 66997196HCID 66997196, compound

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-trans-4-fluoro-L-proline 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 8.65-8.59 (m, 1H), 8.33 (d, J=7.5 Hz, 1H), 7.67 (dd, J=8.9, 2.5 Hz, 1H), 6.36 (d, J=8.9 Hz, 1H), 5.20 (dt, J=54.4, 3.5 Hz, 1H), 4.36-4.23 (m, 2H), 3.75 (d, J=8.4 Hz, 1H), 3.66-3.52 (m, 3H), 3.30 (dt, J=15.2, 7.6 Hz, 2H), 2.91 (dd, J=38.5, 11.2 Hz, 1H), 2.77-2.68 (m, 1H), 2.68-2.52 (m, 2H), 2.25 (dddd, J=39.3, 14.8, 7.9, 4.4 Hz, 1H), 2.11 (ddd, J=19.5, 7.2, 4.9 Hz, 1H), 1.92 (dtd, J=13.0, 8.1, 4.8 Hz, 1H), 1.62 (dq, J=12.7, 8.2 Hz, 1H), 1.39 (dtd, J=13.4, 7.9, 5.7 Hz, 1H); MS (ESI+) m/z 387 (M+H)+.

Sources & evidence

ORD record
ord-42e0343d832848718b4582693ffa7590
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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