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

HRID 1034628Notes

Reaction equation

HRID 1034628 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-40df470a548f45ae99515f1c2cc6df13
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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