(R)-1-Cbz-2-(aminocarbonyl)piperidine → 2-Piperidinecarboxamide, (R)-

HRID 1155088Notes

Reaction equation

HRID 1155088 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([NH2:5])=[O:4]>CO.[Pd]>[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([NH2:5])=[O:4]

Participants

4

Reactant 1

HCID 27281977(R)-1-Cbz-2-(aminocarbonyl)piperidine

Product 1

HCID 70621612-Piperidinecarboxamide, (R)-Yield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.93 g (15 mmoles) of Z-D-Pip-NH2 are dissolved in 75 ml of methanol, 0.5 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for one hour. The catalyst is filtered off, the filtrate is evaporated, and the residue is triturated with ether. 1.70 g (90%) of H-D-Pip-NH2 are obtained: m.p.: 161°-163° C., Rf4 =0.10, [α]D25 =+31.0° (c=1%, in methanol).

Workup

  1. customhydrogen is bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe residue is triturated with ether

Sources & evidence

ORD record
ord-7dd3a3e75d6742c6a4f17365b3891bef
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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