Methylglyoxal → HCID 11424665, compound

HRID 1979081Notes

Reaction equation

HRID 1979081 reaction equation
[CH:1](=O)[C:2]([CH3:4])=[O:3].[NH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:8]1>CCOCC>[O:3]=[C:2]([CH3:4])[CH:1]=[N:6][CH:7]1[CH2:8][CH2:9][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 880MethylglyoxalHCID 100867Ethyl 4-amino-1-piperidinecarboxylate

Product 1

HCID 11424665HCID 11424665, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of pyruvaldehyde (40% w/w solution in water, 2.67 mL, 3.15 g, 17.5 mmol) in 50 mL of Et2O at room temperature was added dropwise ethyl 4-amino-piperidinecarboxylate (3.0 mL, 3.01 g, 17.5 mmol). After 20 min, the solution was diluted with 50 mL of Et2O and washed with 3×30 mL of water. The solution was concentrated in vacuo to yield 2.3 g (58%) of the imine product which was used as such in the subsequent step: 1H NMR (CDCl3) δ 7.58 (1H, s), 4.07 (2H, q, J=7.1 Hz), 4.04 (2H, m), 3.39 (1H, m), 3.02 (2H, m), 2.31 (3H, s), 1.65 (4H, m), 1.19 (3H, t, J=7.1 Hz).

Workup

  1. washwashed with 3×30 mL of water
  2. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-3363bc96e2b44bbbb0a07bb4d14984cb
Source dataset
uspto-grants-2001_05
Patent number
US06239279B1

Reaction notes

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