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

HRID 1593468Notes

Reaction equation

HRID 1593468 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+]>CO.[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 11080151(3R,4R)-1-tert-butyl 3-ethyl 4-((R)-1-phenylethylamino)-piperidine-1,3-dicarboxylate

Product 1

HCID 58745614(3R,4R)-1-tert-butyl 3-ethyl 4-aminopiperidine-1,3-dicarboxylateYield 96.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 252D (1.18 g, 3.13 mmol) in MeOH (31 mL) was treated with ammonium formate (1.58 g, 25.1 mmol) and 10% Pd/C. The reaction mixture was heated to reflux for 14 hours then cooled to room temperature. The resulting solid was removed by filtration and washed with MeOH. The filtrate was dried (Na2SO4) and concentrated under reduced pressure to give 0.82 g (yield: 96%) of Compound 252E as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 14 hours
  3. customThe resulting solid was removed by filtration
  4. washwashed with MeOH
  5. dry with materialThe filtrate was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-080a6bbcc21c46389f8dbc61b8d99ce3
Source dataset
uspto-grants-2007_11
Patent number
US07297695B2

Reaction notes

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