1,1-Dimethylethyl (3R,4R)-4-azido-3-hydroxy-1-piperidinecarboxylate → rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

HRID 402084Notes

Reaction equation

HRID 402084 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([N:14]=[N+]=[N-])[C@H:10]([OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([NH2:14])[C@H:10]([OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 587455301,1-Dimethylethyl (3R,4R)-4-azido-3-hydroxy-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 10727458rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (±)-trans-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (10 mmol, 2.42 g) in methanol (25 mL) was added 10% palladium on carbon (0.5 g, wet), and the resultant reaction mixture was subjected to hydrogenation using a balloon full of hydrogen for 8 h. The catalyst was filtered through a pad of celite, and the pad was with methanol (25 mL). The combined filtrate was concentrated under reduced pressure to provide (±)-trans-4-amino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customthe resultant reaction mixture
  2. customfor 8 h
  3. filtrationThe catalyst was filtered through a pad of celite
  4. concentrationThe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6a5131de90b3425dbd3814e8020e89d5
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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