Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate → 4-(N-Boc-amino)piperidine

HRID 482565

Reaction equation

HRID 482565 reaction equation
C([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]1)(OCC1C=CC=CC=1)=O>C(O)C.[Pd]>[C:18]([NH:17][CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

4

Reactant 1

HCID 21981786Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

Product 1

HCID 7238334-(N-Boc-amino)piperidineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-CBZ-4-(BOC-amino)-piperidine (3.0 g, 9.0 mmol) was dissolved in ethanol (100 mL) and transferred into a Parr shaker bottle. After adding 10% palladium on carbon (0.5 g), the mixture was shaken under an atmosphere of hydrogen at 50 psi for 0.75 h on a Parr apparatus. The catalyst was removed by filtration through a pad of Celite. The filter cake was washed with ethanol and the combined filtrate and washings were concentrated in vacuo to yield 1.8 g (100%) of crude 4-(BOC-amino)-piperidine as a pale yellow oil. This product was used immediately in the next step without further purification.

Workup

  1. customThe catalyst was removed by filtration through a pad of Celite
  2. washThe filter cake was washed with ethanol
  3. concentrationthe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-e44a2a2a49a9468baf915e63b5283c87
Source dataset
uspto-grants-1998_08
Patent number
US05798337

Linked notes

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