(NE,S)-N-[(3aS,6aR)-2-benzyl-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrol-4-ylidene]-2-methylpropane-2-sulfinamide → (3aS,4R,6aR*)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine

HRID 1092536Notes

Reaction equation

CC([S@@](/[N:7]=[C:8]1\[CH2:9][CH2:10][C@@H:11]2[C@H:15]\1[CH2:14][N:13]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)[CH2:12]2)=O)(C)C.C(N1C[C@H]2/C(=N/[S@](C(C)(C)C)=O)/CC[C@H]2C1)C1C=CC=CC=1>>[F:25][C:23]([F:24])([F:26])[C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[CH2:16][N:13]1[CH2:14][C@H:15]2[C@H:8]([NH2:7])[CH2:9][CH2:10][C@H:11]2[CH2:12]1

Participants

Reactant 2

HCID 87063931(NE,S)-N-[(3aS,6aR)-2-benzyl-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrol-4-ylidene]-2-methylpropane-2-sulfinamide

HCID 87063947(NE,S)-N-[(3aS,6aR)-2-[[3-(trifluoromethyl)phenyl]methyl]-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrol-4-ylidene]-2-methylpropane-2-sulfinamide

Product 1

HCID 66590435(3aS*,4R*,6aR*)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine

Procedure

(3aS,4R,6aR)-2-(3-(Trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine was prepared according to the procedure described in Example 16 Steps A-E substituting (S,E)-2-methyl-N-((3aS,6aR)-2-(3-(trifluoromethyl)benzyl)hexahydrocyclopenta[c]pyrrol-4(5H)-ylidene)propane-2-sulfinamide from Step A in Example 152 for (S,E)-N-((3aS,6aR)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-ylidene)-2-methylpropane-2-sulfinamide in Step A-E of Example 16 to give (3 aS,4R,6aR)-2-(3-(trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.78 (s, 1H), 7.59 (d, J=6.0, 2H), 7.45 (t, J=7.7, 1H), 4.94 (br s, 2H), 3.53 (s, 2H), 3.13 (dd, J=5.1, 11.6, 1H), 2.63-2.54 (m, 1H), 2.49 (dd, J=3.3, 9.0, 1H), 2.35 (dd, J=7.5, 9.0, 1H), 2.32 (d, J=5.9, 2H), 2.21-2.13 (m, 1H), 1.96 (dt, J=6.0, 8.7, 1H), 1.88 (td, J=3.9, 9.7, 1H), 1.38-1.29 (m, 2H); MS (ESI+) m/z 284 (M+H)+.

Workup

custom(3aS,4R,6aR)-2-(3-(Trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine was prepared

Sources & evidence

ORD record: ord-19c65543d4ab45798a927d4a30d6e9eb
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129417B2

Reaction notes

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