(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine → HCID 66997489, compound

HRID 2363661Notes

Reaction equation

HRID 2363661 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: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>>[CH:14]1([CH2:13][C@@H:9]([C:10]([NH:36][C@@H:33]2[C@@H:31]3[C@@H:30]([CH2:29][N:28]([C:25]4[CH:24]=[CH:23][C:22]([O:21][C:20]([F:38])([F:19])[F:37])=[CH:27][CH:26]=4)[CH2:32]3)[CH2:35][CH2:34]2)=[O:12])[NH:8][CH3:18])[CH2:16][CH2:17]1

Participants

4

Reactant 3

HCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66997100HCID 66997100, compoundHCID 86641984N-Boc-N-methyl-3-tert-butyl-L-alanine

Product 1

HCID 66997489HCID 66997489, compound

Procedure

The title compound was prepared by substituting 3-cyclopropyl-N-(tert-butoxycarbonyl)-N-methyl-L-alanine 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) δ ppm 8.28 (d, J=7.6, 1H), 7.22 (s, 2H), 6.65-6.54 (m, 2H), 4.46-4.36 (m, 1H), 3.55 (dd, J=9.9, 2.7, 1H), 3.35-3.24 (m, 2H), 3.15 (dd, J=9.5, 7.8, 1H), 3.02 (dd, J=9.6, 3.3, 1H), 2.79-2.67 (m, 2H), 2.46 (d, J=9.2, 3H), 2.17-2.05 (m, 1H), 2.02-1.91 (m, 1H), 1.84 (dd, J=30.5, 23.8, 1H), 1.83-1.62 (m, 3H), 1.45-1.35 (m, 1H), 0.99-0.86 (m, 1H), 0.53-0.38 (m, 2H), 0.19-0.07 (m, 2H); MS (ESI+) m/z 412 (M+H)+.

Sources & evidence

ORD record
ord-d8c5036cdf264ed1908089fe1900896c
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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