Methyl(4S)-5-azido-4-[(tert-butoxy)carbonylamino]pentanoate → (S)-tert-butyl 6-oxopiperidin-3-ylcarbamate

HRID 2356266Notes

Reaction equation

HRID 2356266 reaction equation
[N:1]([CH2:4][C@@H:5]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:7][C:8](OC)=[O:9])=[N+]=[N-].[H][H]>CO.[Pd]>[O:9]=[C:8]1[NH:1][CH2:4][C@@H:5]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 10778574Methyl(4S)-5-azido-4-[(tert-butoxy)carbonylamino]pentanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 15466433(S)-tert-butyl 6-oxopiperidin-3-ylcarbamateYield 99.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl (4S)-5-azido-4-[(tert-butoxy)carbonylamino]pentanoate (3.9 mmol, 1.07 g) was dissolved in methanol (10 mL), and 10% palladium on carbon (0.1 g) was added. The reaction was stirred overnight under 1 atm of hydrogen. The reaction was filtered and the solvent was removed in vacuo to yield the title compound (0.83 g, 99% yield). ES-MS: 215 (M+1).

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-99e0edc0e46547adb588cf1726c15c79
Source dataset
uspto-grants-2010_07
Patent number
US07759342B2

Reaction notes

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