(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → HCID 66997446, compound

HRID 2363646Notes

Reaction equation

C(O[C:6]([N:8](C)[C@@H:9]([CH2:13][C:14](C)(C)[CH3:15])[C:10](O)=[O:11])=O)(C)(C)C.[F:19][C:20]([F:38])([F:37])[O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH2:32][C@@H:31]3[C@@H:33]([NH2:36])[CH2:34][CH2:35][C@@H:30]3[CH2:29]2)=[CH:24][CH:23]=1.FC(F)(F)C1N=C(N2C[C@@H]3[C@@H](N)CC[C@@H]3C2)C=CC=1>>[CH3:6][NH:8][C@H:9]([C:10]([NH:36][C@@H:33]1[C@@H:31]2[C@@H:30]([CH2:29][N:28]([C:25]3[CH:24]=[CH:23][C:22]([O:21][C:20]([F:19])([F:37])[F:38])=[CH:27][CH:26]=3)[CH2:32]2)[CH2:35][CH2:34]1)=[O:11])[CH2:13][CH2:14][CH3:15]

Participants

Reactant 3

HCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine

HCID 66997100HCID 66997100, compound

HCID 86641984N-Boc-N-methyl-3-tert-butyl-L-alanine

Product 1

HCID 66997446HCID 66997446, compound

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-norvaline for (S)-2-(tert-butoxycarbonyl(methyl)amino)-4,4-dimethylpentanoic acid and (3aR,4S,6aS)-2-(4-(trifluoromethoxy)phenyl)octahydrocyclopenta[c]pyrrol-4-amine from Example 716 Step 1 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, temperature 90° C.) δ ppm 7.60-7.71 (m, 1H), 7.10-7.15 (m, 2H), 6.56-6.59 (m, 2H), 4.24-4.32 (m, 1H), 3.47 (dd, J=9.9, 3.6 Hz, 1H), 3.31 (dd, J=9.8, 7.9 Hz, 1H), 3.19 (dd, J=9.5, 7.9 Hz, 1H), 3.10 (dd, J=6.9, 5.8 Hz, 1H), 3.01 (dd, J=9.6, 4.0 Hz, 1H), 2.71-2.83 (m, 1H), 2.56-2.70 (m, 1H), 2.40 (s, 3H), 2.09 (dq, J=12.6, 6.3 Hz, 1H), 1.92-2.01 (m, 1H), 1.74-1.83 (m, 1H), 1.58-1.70 (m, 2H), 1.38-1.53 (m, 3H), 0.88 (t, J=7.3 Hz, 3H); MS (ESI+) m/z 400 (M+H)+.

Sources & evidence

ORD record: ord-fc57ecd4a0b047e08491c1d24099779f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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