(2R,4R)-1-tert-butyl 2-methyl 4-azidopiperidine-1,2-dicarboxylate → (2R,4R)-1-tert-butyl 2-methyl 4-aminopiperidine-1,2-dicarboxylate

HRID 1685458Notes

Reaction equation

HRID 1685458 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:6]([C:17]([O:19][CH3:20])=[O:18])[CH2:5]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C@@H:6]([C:17]([O:19][CH3:20])=[O:18])[CH2:5]1

Participants

4

Reactant 1

HCID 54053444(2R,4R)-1-tert-butyl 2-methyl 4-azidopiperidine-1,2-dicarboxylate

Product 1

HCID 54209755(2R,4R)-1-tert-butyl 2-methyl 4-aminopiperidine-1,2-dicarboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2R,4R)-1-tert-butyl 2-methyl 4-azidopiperidine-1,2-dicarboxylate (22.5 g, 79 mmol) was dissolved in methanol (400 mL), Pd/C (10%, 6 g) was added, and the apparatus was flushed three times with N2 and H2. The reaction mixture was hydrogenated at a pressure of 50 psi at room temperature for 20 hours, filtered through Celite and rinsed with methanol and then concentrated under reduced pressure to give the amine as a colorless oil 20 g (96%). GC-MS: 258 (t=2.8 min).

Workup

  1. customthe apparatus was flushed three times with N2 and H2
  2. filtrationfiltered through Celite
  3. washrinsed with methanol
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6368dc771c24e2bba31a857dd21f3bf
Source dataset
uspto-grants-2012_04
Patent number
US08148401B2

Reaction notes

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