(3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester → rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

HRID 2066541Notes

Reaction equation

HRID 2066541 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]>C(O)C.[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

4

Reactant 1

HCID 58745530(3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 10727458rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylateYield 103.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (3R*,4R*)-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.96 g, 12.23 mmol) in ethanol (50 mL) was flushed out with nitrogen. Palladium (10 wt % on activated carbon) (˜300 mg) was added and the mixture flushed out with hydrogen and then stirred under a hydrogen balloon at room temperature overnight. The reaction mixture was filtered through celite and the filtrate evaporated to give (3R*,4R*)-4-amino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2.73 g).

Workup

  1. customthe mixture flushed out with hydrogen
  2. filtrationThe reaction mixture was filtered through celite
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-7f3051a3008d4cdf9c4f6898c9a3bceb
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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