3-Furancarboxaldehyde, tetrahydro- → HCID 86608736, compound

HRID 2113605Notes

Reaction equation

HRID 2113605 reaction equation
CC([CH:5]1[C@@H:10]([NH2:11])[CH2:9][CH2:8][CH2:7][N:6]1[C:12]([O-:14])=[O:13])(C)C.[O:15]1[CH2:19][CH2:18][CH:17]([CH:20]=O)[CH2:16]1>[Pd].C(O)C>[O:15]1[CH2:19][CH2:18][CH:17]([CH2:20][NH:11][C@H:10]2[CH2:9][CH2:8][CH2:7][N:6]([C:12]([O:14][C:17]([CH3:20])([CH3:18])[CH3:16])=[O:13])[CH2:5]2)[CH2:16]1

Participants

5

Reactant 2

HCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 86608737HCID 86608737, compound

Product 1

HCID 86608736HCID 86608736, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 5% palladium on carbon (0.05 g) under nitrogen was added a solution of 1,1-dimethylethyl-(3S)-3-aminopiperidine-1-carboxylate (0.50 g, 2.5 mmol) and tetrahydrofuran-3-carboxaldehyde (50% w/w in water) (0.50 g, 2.5 mmol) in ethanol (20 mL). The reaction mixture was hydrogenated overnight at 60 psi in a Parr hydrogenator. The catalyst was removed by filtration through Celite and the solvent removed in vacuo to give 1,1-dimethylethyl (3S)-3-[(tetrahydrofuran-3-ylmethyl)amino]piperidine-1-carboxylate as a colourless, slightly cloudy oil.

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-38ead057f5fe4025b7206aaf17f56a70
Source dataset
uspto-grants-2008_10
Patent number
US07432280B2

Reaction notes

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