(2S)-N-[(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methylpentanamide → (2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methyl-N-[(3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]pentanamide

HRID 2363596Notes

Reaction equation

HRID 2363596 reaction equation
C([N:8]1[CH2:12][C@H:11]2[C@H:13]([NH:16][C:17](=[O:30])[C@@H:18]([N:23]3[CH2:27][CH2:26][CH2:25][S:24]3(=[O:29])=[O:28])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[O:29]=[S:24]1(=[O:28])[CH2:25][CH2:26][CH2:27][N:23]1[C@@H:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:17]([NH:16][C@H:13]1[C@H:11]2[C@H:10]([CH2:9][NH:8][CH2:12]2)[CH2:15][CH2:14]1)=[O:30]

Participants

5

Reactant 2

HCID 66590193(2S)-N-[(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methylpentanamideHCID 178418361HCID 178418361, compound

Product 1

HCID 66590695(2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methyl-N-[(3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]pentanamide

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(2S)-N-[(3aS,4R,6aR)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-yl]-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methylpentanamide (265 mg, 0.611 mmol) from Example 220 Step D and ethanol (20 mL) were added to 20% Pd(OH)2 on carbon, wet (53.0 mg, 0.377 mmol) in a 50 mL pressure bottle and stirred for 48 hours under 30 psi hydrogen at 50° C. The mixture was filtered through a nylon membrane and the solvent removed in vacuo to give (2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methyl-N-[(3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]pentanamide: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.89 (dd, J=6.6, 18.9, 1H), 4.55-4.50 (m, 1H), 4.42-4.31 (m, 1H), 3.99-3.91 (m, 1H), 3.44-3.39 (m, 1H), 3.34 (dd, J=2.8, 11.4, 0.5H), 3.29-3.25 (m, 2H), 3.21 (dd, J=5.4, 13.2, 1H), 3.13 (dd, J=7.7, 11.2, 0.5H), 2.99 (td, J=7.5, 10.8, 1H), 2.79 (dd, J=3.3, 10.9, 0.5H), 2.73 (dd, J=3.3, 10.9, 0.5H), 2.69-2.55 (m, 2H), 2.31-2.16 (m, 2H), 2.12-2.00 (m, 1H), 1.94-1.78 (m, 4H), 1.69 (dddd, J=5.2, 11.0, 16.7, 19.8, 2H), 1.49-1.29 (m, 1H), 0.88 (t, J=6.5, 3H), 0.83 (t, J=6.4, 3H); MS (ESI+) m/z 344 (M+H)+

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4b737b1aed6544db8e6ab631923de20e
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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