HCID 54674009, compound → HCID 66591198, compound

HRID 2363598Notes

Reaction equation

HRID 2363598 reaction equation
C([N:8]1[CH2:12][C@H:11]2[C@H:13]([NH:16][C:17](=[O:29])[C@@H:18]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[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>[CH3:21][CH:20]([CH3:22])[CH2:19][C@H:18]([N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1)[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:29]

Participants

5

Reactant 2

HCID 54674009HCID 54674009, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66591198HCID 66591198, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(S)-N-((3aS,4R,6aR)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-yl)-4-methyl-2-morpholinopentanamide (0.400 g, 1.001 mmol) from Step B of Example 249 and ethanol (40 mL) were added to 20% Pd(OH)2 on carbon, wet (0.080 g, 0.570 mmol) in a 250 mL stainless steel pressure bottle and stirred for 16 hours under 30 psi hydrogen at 55° C. The mixture was filtered through a nylon membrane and the solvent removed in vacuo to give (S)-4-methyl-2-morpholino-N-((3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl)pentanamide: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.46 (d, J=6.9, 1H), 4.46-4.38 (m, 1H), 3.74 (s, 4H), 3.45 (dd, J=2.0, 11.3, 1H), 3.31-3.21 (m, 2H), 3.10 (dd, J=7.0, 11.0, 1H), 2.89 (dd, J=2.3, 11.0, 1H), 2.83-2.77 (m, 2H), 2.76-2.67 (m, 4H), 2.09 (td, J=6.0, 11.8, 1H), 1.95-1.87 (m, 1H), 1.84 (dq, J=6.0, 9.7, 2H), 1.71-1.57 (m, 2H), 1.49 (ddt, J=6.3, 9.1, 12.5, 1H), 0.94 (dd, J=6.3, 11.2, 6H); MS (ESI+) m/z 310 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-5672d5e153b5421bb1929d873d28fc62
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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