HCID 86657828, compound → HCID 67372431, compound

HRID 402063Notes

Reaction equation

HRID 402063 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH:10]([CH2:16][N:17]=[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]([O:14][CH3:15])[CH:10]([CH2:16][NH2:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 86657828HCID 86657828, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67372431HCID 67372431, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-azidomethyl-4-methoxy-piperidine-1-carboxylic acid tert-butyl ester (0.74 mmol, 0.2 g) in ethyl acetate (5 mL) was added 10% palladium on carbon (0.1 g, wet), and the resultant reaction mixture was subjected to hydrogenation using a balloon full of hydrogen for 1 h. The catalyst was filtered through a pad of celite, washed the celite pad with methanol, and the combined filtrate was concentrated under reduced pressure to provide 3-aminomethyl-4-methoxy-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customthe resultant reaction mixture
  2. customfor 1 h
  3. filtrationThe catalyst was filtered through a pad of celite
  4. washwashed the celite pad with methanol
  5. concentrationthe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2552e1a587e24a1e9851ac750cca2957
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

Loading…