Acetic Acid → tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylate

HRID 1013080Notes

Reaction equation

HRID 1013080 reaction equation
C(OC([NH:11][C:12]1([C:25](=[O:27])[NH2:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=O)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[NH2:11][C:12]1([C:25](=[O:27])[NH2:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 10714606tert-Butyl 4-(((benzyloxy)carbonyl)amino)-4-carbamoylpiperidine-1-carboxylate

Product 1

HCID 10562199tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1B (1.0 equivalent) and a catalytic amount of acetic acid in MeOH (0.05M) was passed through H-cube hydrogenator equipped with Pd/C cartridge at 50° C. The methanol in the reaction mixture was then removed under reduced pressure, and the product was washed with cold ether twice to afford the tert-butyl 4-amino-4-carbamoylpiperidine-1-carboxylate (1C, 90%).

Workup

  1. customThe methanol in the reaction mixture was then removed under reduced pressure
  2. washthe product was washed with cold ether twice

Sources & evidence

ORD record
ord-367907cef00340c4bafce33b32861342
Source dataset
uspto-grants-2011_07
Patent number
US07981904B2

Reaction notes

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