(R)-1-Cbz-3-(Boc(ethyl)amino)piperidine → (R)-3-[Boc(ethyl)amino]piperidine

HRID 2203699Notes

Reaction equation

HRID 2203699 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:25][CH3:26])[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.CO.[Pd].CCO>[CH2:25]([N:8]([C@@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH3:26]

Participants

5

Reactant 1

HCID 86652139(R)-1-Cbz-3-(Boc(ethyl)amino)piperidine

Product 1

HCID 58195511(R)-3-[Boc(ethyl)amino]piperidine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

A solution of (R)-benzyl 3-(tert-butoxycarbonyl(ethyl)amino)piperidine-1-carboxylate (5.00 g, 13.8 mmol) in a mixture of EtOH:MeOH (1:1, 50 mL) was added to a suspension of 10% palladium on activated carbon (1.47 g, 1.38 mmol) in EtOH (20 mL) under N2 atmosphere. The mixture was degassed under N2 (3 cycles) and back filled with H2 (3 cycles) using a H2 balloon. The mixture was then stirred under H2 atmosphere for 4 hours. The reaction mixture was then filtered through a pad of celite washing with 5% MeOH/EtOAc (3×30 mL). The filtrate collected was concentrated in vacuo to provide the crude (R)-tert-butyl ethyl(piperidin-3-yl)carbamate. LCMS (APCI+) m/z 229 (M+H)+.

Workup

  1. customThe mixture was degassed under N2 (3 cycles)
  2. additionback filled with H2 (3 cycles)
  3. filtrationThe reaction mixture was then filtered through a pad of celite
  4. washwashing with 5% MeOH/EtOAc (3×30 mL)
  5. customThe filtrate collected
  6. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-b0009ea7fa9940dcbdcf72f7254393ca
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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