HCID 72447677, compound → HCID 67373104, compound

HRID 1972067Notes

Reaction equation

HRID 1972067 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][N:16]=[N+]=[N-])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][NH2:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 72447677HCID 72447677, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67373104HCID 67373104, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-azidomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.624 mmol, 0.16 g) in ethyl acetate (5 mL) was added 10% palladium on carbon (0.1 g, wet). The resultant reaction mixture was subjected to hydrogenation using a balloon full of hydrogen for 4 h. The catalyst was filtered through a pad of celite and the filtrate was concentrated to provide 3-aminomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe resultant reaction mixture
  2. customfor 4 h
  3. filtrationThe catalyst was filtered through a pad of celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9c108fd6c8884518af8e1fc70fd8de43
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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