tert-Butyl cis-5-azido-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidine-1-carboxylate → tert-Butyl cis-5-amino-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidine-1-carboxylate

HRID 602454Notes

Reaction equation

HRID 602454 reaction equation
[N:1]([C@H:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:7]([CH2:17][C:18]2([OH:24])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH2:6][CH2:5]1)=[N+]=[N-]>[Pd].CO>[NH2:1][C@H:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[C@@H:7]([CH2:17][C:18]2([OH:24])[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 86624147tert-Butyl cis-5-azido-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidine-1-carboxylate

Product 1

HCID 67269815tert-Butyl cis-5-amino-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture of tert-butyl cis-5-azido-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidine-1-carboxylate (253 mg, 0.743 mmol, step 4 of Example 2) and 10 wt. % palladium on carbon (50 mg) in methanol (5 mL) was stirred under hydrogen (4 atom) at room temperature for 7 h. The mixture was filtered through a pad of Celite washing with methanol and the filtrate was concentrated to give 244 mg (quant.) of the title compound as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashing with methanol
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dd86276b187b4f44b877a4eef48252ff
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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