Ammonium formate → 1-tert-butyl 3-ethyl (3S,4R)-4-aminopiperidine-1,3-dicarboxylate

HRID 723478Notes

Reaction equation

HRID 723478 reaction equation
C1([C@H]([NH:9][C@@H:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@@H:11]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])C)C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:9][C@@H:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12][C@@H:11]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 66952586(3S,4R)-1-tert-butyl 3-ethyl 4-((R)-1-phenylethylamino)-piperidine-1,3-dicarboxylate

Product 1

HCID 587454941-tert-butyl 3-ethyl (3S,4R)-4-aminopiperidine-1,3-dicarboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 252C (2.6 g, 6.9 mmol) in EtOH (100 mL) was treated with ammonium formate (3.5 g, 55.3 mmol) and 10% Pd/C (390 mg). The reaction mixture was heated to reflux under a nitrogen atmosphere for three hours. The resulting suspension was filtered through a pad of celite and concentrated in vacuo to afford 1.8 g (yield: 96%) Compound 259A as a solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under a nitrogen atmosphere for three hours
  3. filtrationThe resulting suspension was filtered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e81da44e67994ff0b1f11b26b4e7da9a
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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