Methylglyoxal → HCID 10584590, compound

HRID 1871085Notes

Reaction equation

HRID 1871085 reaction equation
[CH:1](=O)[C:2]([CH3:4])=[O:3].[CH3:6][C:7]1([CH3:16])[CH2:12][CH:11]([NH2:13])[CH2:10][C:9]([CH3:15])([CH3:14])[NH:8]1>CC(OC)(C)C>[CH3:6][C:7]1([CH3:16])[CH2:12][CH:11]([N:13]=[CH:1][C:2](=[O:3])[CH3:4])[CH2:10][C:9]([CH3:15])([CH3:14])[NH:8]1

Participants

4

Reactant 2

HCID 880MethylglyoxalHCID 375244-Amino-2,2,6,6-tetramethylpiperidine

Product 1

HCID 10584590HCID 10584590, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a solution of pyruvaldehyde (40% w/w solution in water, 2.68 mL, 3.16 g, 17.5 mmol) in 30 mL of TBME at room temperature was added dropwise 2,2,6,6-tetramethyl-4-amino-piperidine (2.0 mL, 2.19 g, 14.0 mmol). After 30 min, the solution was diluted with 50 mL of TBME and washed with 3×25 mL of water and 25 mL of brine. The solution was concentrated in vacuo to yield 2.1 g (71%) of the imine product which was used as such in the subsequent step: 1H NMR (CDCl3) δ 7.64 (1H, s), 3.70 (1H, tt, J=3.9, 11.6 Hz), 2.34 (3H, s), 1.61 (2H, dd, J=3.9, 13.0 Hz), 1.32 (2H, t, J=12.2 Hz), 1.21 (6H, s), 1.14 (6H, s).

Workup

  1. washwashed with 3×25 mL of water and 25 mL of brine
  2. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-ca19d54bedb645708b538e317d153ad7
Source dataset
uspto-grants-2000_08
Patent number
US06100399

Reaction notes

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