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

HRID 2363451Notes

Reaction equation

[CH2:1]([N:8]1[CH2:12][C@@H:11]2/[C:13](=[N:16]/[S@](C(C)(C)C)=O)/[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C[C@H]2/C(=N/[S@](C(C)(C)C)=O)/CC[C@H]2C1)C1C=CC=CC=1>>[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH2:16])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 87063925(NE,S)-N-[(3aR,6aS)-2-benzyl-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrol-4-ylidene]-2-methylpropane-2-sulfinamide

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

Product 1

HCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Procedure

(3aR,4S,6aS)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-amine was prepared according to the procedure described in Example 16 Steps A-E substituting (S,E)-N-((3aR,6aS)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-ylidene)-2-methylpropane-2-sulfinamide from Step A in Example 14 for (S,E)-N-((3aS,6aR)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-ylidene)-2-methylpropane-2-sulfinamide in Step A of Example 16 to give (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine: 1H NMR (300 MHz, CDCl3) δ ppm 7.34-7.28 (m, 4H), 7.25-7.18 (m, 1H), 3.54 (s, 2H), 3.09 (dd, J=4.8, 10.9, 1H), 2.75-2.58 (m, 1H), 2.48 (dd, J=8.6, 16.5, 2H), 2.40 (dd, J=3.9, 9.3, 1H), 2.30 (dd, J=3.9, 9.0, 1H), 2.21-2.09 (m, 1H), 2.01-1.84 (m, J=6.9, 12.0, 2H), 1.47-1.25 (m, 4H).

Workup

custom(3aR,4S,6aS)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-amine was prepared

Sources & evidence

ORD record: ord-7da40fbdad5d4665ae47b032ec88cbd4
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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