(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → HCID 86659293, compound

HRID 2363654Notes

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:26]=[CH:25][C:24]([N:27]2[CH2:31][C@@H]3[C@@H](N)CC[C@@H]3C2)=[CH:23][CH:22]=1.F[C:39](F)(F)[C:40]1[N:45]=[C:44](N2C[C@@H]3[C@@H](N)CC[C@@H]3C2)C=C[CH:41]=1>>[CH3:44][NH:45][C:40]([CH3:41])([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][CH:25]=3)[CH2:31]2)[CH2:17][CH2:10]1)=[O:7])[CH3:39]

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 86659293HCID 86659293, compound

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N,2-dimethyl-L-alanine 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 7.95 (d, J=7.5, 1H), 7.57 (d, J=8.7, 2H), 6.61 (d, J=8.7, 2H), 4.33-4.21 (m, 1H), 3.50 (dd, J=10.2, 3.6, 1H), 3.33 (dd, J=10.1, 8.0, 1H), 3.21 (dd, J=9.7, 8.3, 1H), 3.00 (dd, J=9.9, 4.2, 1H), 2.75-2.65 (m, 1H), 2.65-2.55 (m, 1H), 2.32 (s, 3H), 2.06 (ddd, J=19.3, 7.0, 5.1, 1H), 2.04-1.96 (bs, 1H), 1.98-1.85 (m, 1H), 1.65-1.53 (m, 1H), 1.44 (s, 3H), 1.42 (s, 3H), 1.40-1.30 (m, 1H); MS (ESI+) m/z 370 (M+H)+.

Sources & evidence

ORD record: ord-1a1e9d7590364d09a57ddd455546d686
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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