HCID 59165785, compound → HCID 58864521, compound

HRID 1442907Notes

Reaction equation

HRID 1442907 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:27]([O-])=O)=[C:6]([CH:26]=1)[CH2:7][C:8]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1>[Pd].CCO>[NH2:27][C:5]1[CH:4]=[CH:3][CH:2]=[CH:26][C:6]=1[CH2:7][C:8]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 59165785HCID 59165785, compound

Product 1

HCID 58864521HCID 58864521, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (200 mg) was added to a solution of 1-tert-butyl 4-ethyl 4-(5-chloro-2-nitrobenzyl)piperidine-1,4-dicarboxylate (250 mg, 0.586 mmol) in EtOH (15 mL). The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (55 psi). After 24 h, the mixture was filtered though celite and concentrated to give the title compound (0.20 g). MS: m/z=363.1 (M+1).

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (55 psi)
  4. filtrationthe mixture was filtered though celite and
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f9a82ab3662e433bb6aa093571dd6850
Source dataset
uspto-grants-2010_02
Patent number
US07659264B2

Reaction notes

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