1-Benzyl 4-tert-butyl piperidine-1,4-dicarboxylate → Tert-butyl Piperidine-4-carboxylate

HRID 906044Notes

Reaction equation

HRID 906044 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:6][CH2:5][CH:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][CH2:2]1>CCOC(C)=O.[Pd]>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 15126991-Benzyl 4-tert-butyl piperidine-1,4-dicarboxylate

Product 1

HCID 1512676Tert-butyl Piperidine-4-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyl 4-tert-butyl piperidine-1,4-dicarboxylate in EtOAc (0.1 M), a catalytic amount of Pd/C (5%) was added and the atmosphere in the reaction vessel charged with H2 (1 atmosphere). The reaction mixture was stirred vigorously at RT for 8 h. The solution was filtered and the filtrate concentrated in vacuo to afford the title compound (76%); MS (ES+) m/z 186(M+H)+

Workup

  1. additionthe atmosphere in the reaction vessel charged with H2 (1 atmosphere)
  2. filtrationThe solution was filtered
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e103021059e74da188693bd674f77f05
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

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