1-tert-Butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate → 1-tert-Butyl 4-ethyl 4-(aminomethyl)piperidine-1,4-dicarboxylate

HRID 423028

Reaction equation

HRID 423028 reaction equation
[C:1]([C:3]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2]>C(O)(=O)C.[Pt](=O)=O>[NH2:2][CH2:1][C:3]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])[CH2:7][CH2:8]1

Participants

4

Reactant 1

HCID 577503761-tert-Butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate2×

Product 1

HCID 468399351-tert-Butyl 4-ethyl 4-(aminomethyl)piperidine-1,4-dicarboxylateYield 83.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Platinum(IV) oxide (0.724 g, 3.19 mmol) and 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate (Intermediate 7) (9 g, 31.9 mmol) in acetic acid (100 ml) were stirred under an atmosphere of hydrogen at 5 bar and 25° C. for 1 day. The crude product was filtered through celite and the filtrate purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford 1-tert-butyl 4-ethyl 4-(aminomethyl)piperidine-1,4-dicarboxylate (7.59 g, 83%) as a colourless oil.

Workup

  1. filtrationThe crude product was filtered through celite
  2. customthe filtrate purified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. customwere evaporated to dryness

Sources & evidence

ORD record
ord-b5b7caef13dc454ab83916b36337e3bb
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Linked notes

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