HCID 131732030, compound → HCID 178472531, compound

HRID 337682Notes

Reaction equation

HRID 337682 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([C@@H:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][C@H:10]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:5]=[C:4]([O:27]CC2C=CC=CC=2)[N:3]=1>[Pd].C(O)C>[OH:27][C:4]1[N:3]=[C:2]([CH3:1])[C:7]([CH3:8])=[C:6]([C@@H:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:11][C@H:10]2[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:5]=1

Participants

4

Reactant 1

HCID 131732030HCID 131732030, compound

Product 1

HCID 178472531HCID 178472531, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To an ethanol solution (0.07 M) of trans-1-(1,1-dimethylethyl) 3-ethyl 4-{2,3-dimethyl-6-[(phenylmethyl)oxy]-4-pyridinyl}-1,3-piperidinedicarboxylate (1 eq.) from the previous step was added palladium (10% w/w over carbon, 0.1 eq.). The resulting suspension was evacuated and purged with hydrogen. Under a balloon-filled hydrogen atmosphere, the reaction mixture was stirred at RT for 2 h. The reaction was then quenched with CH2Cl2, filtered through a bed of celite and the insolubles rinsed with EtOAc. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

Workup

  1. customThe resulting suspension was evacuated
  2. custompurged with hydrogen
  3. customThe reaction was then quenched with CH2Cl2
  4. filtrationfiltered through a bed of celite
  5. washthe insolubles rinsed with EtOAc

Sources & evidence

ORD record
ord-e919c00ff8f64ccd8464607e74c80628
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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