Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate → Tert-butyl 4-(3-bromobenzyl)piperidine-1-carboxylate

HRID 564555

Reaction equation

HRID 564555 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1>C1COCC1.[Pd]>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 57813409Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate

Product 1

HCID 57813365Tert-butyl 4-(3-bromobenzyl)piperidine-1-carboxylateYield 94.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-[(3-bromophenyl)methylidene]-1-piperidinecarboxylate (201 mg, 0.571 mmol) in THF (1 mL) was applied onto H-Cube using 10% Pd/C at a flow rate of 1 mL/min and 1 atm H2. The mixture was concentrated to afford 0.1909 g (94%) of the title compound. LC-MS m/z 354 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-df9fe245de054905bacedbd7e7a4ed5f
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Linked notes

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