HCID 67125438, compound → HCID 67971347, compound

HRID 1470736Notes

Reaction equation

HRID 1470736 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][C:23](=[O:26])[CH2:24][CH3:25])[CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]([NH:22][C:23](=[O:26])[CH2:24][CH3:25])[CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 67125438HCID 67125438, compound

Product 1

HCID 67971347HCID 67971347, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

9.58 g (27.5 mmol) ((S)—N-{1-[4-(1-Benzyl-1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-ethyl}-propionamide (XXII.1) in 130 mL ethanol are hydrogenated (3 bar) for 7 h at 50° C. using 0.80 g Pd/C (10%). After that time, the catalyst is filtered off and the solvent is evaporated. The residue is purified by HPLC (column: Gemini Phenomenex, 10 μM; eluent A: water+0.30% NH4OH, eluent B: acetone) to yield the desired product.

Workup

  1. customfor 7 h
  2. customat 50° C.
  3. filtrationAfter that time, the catalyst is filtered off
  4. customthe solvent is evaporated
  5. customThe residue is purified by HPLC (column: Gemini Phenomenex, 10 μM; eluent A: water+0.30% NH4OH, eluent B: acetone)

Sources & evidence

ORD record
ord-6b9f7ae8a7f14d36a2a06f08cedc1235
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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