3-Pentanamine → Dimethyl methylmalonate

HRID 2298435Notes

Reaction equation

HRID 2298435 reaction equation
C[C:2]([CH3:10])([C:7]([O-:9])=[O:8])[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[CH2:13](C(N)CC)C>CS(C)=O>[CH3:6][O:5][C:3](=[O:4])[CH:2]([CH3:10])[C:7]([O:9][CH3:13])=[O:8]

Participants

5

Reactant 3

HCID 120193-PentanamineHCID 24758Sodium hydrideHCID 18386660HCID 18386660, compound

Product 1

HCID 69104Dimethyl methylmalonate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of methyl dimethylmalonate (260 mg) and 60% sodium hydride in oil (70 mg) in 4 ml of DMSO was stirred at room temperature for 10 min. A solution of 3-chloromethyl-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-4-yl]-(1-ethyl-propyl)-amine (200 mg) in 2 ml of DMSO was added. The mixture was stirred at room temperature for 3 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give the crude material which was purified through silica gel using hexane to 10% ethyl acetate in hexane as eluent to give 137 mg of 2-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]methyl]-2-methyl-malonic acid dimethyl ester as a white solid. 1H NMR (CDCl3) δ 6.83(s,2H), 6.01(s,1H), 5.00(m,1H), 3.70(s,6H), 3.40(s,2H), 3.25(m,1H), 2.27(s,3H), 2.12(s,3H), 2.05(s,6H), 1.5-1.7(m,4H), 1.48(s,3H), 0.94(t,6H)ppm.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customto give the crude material which
  7. customwas purified through silica gel

Sources & evidence

ORD record
ord-7409eb2d3e1e46d98403b7b81df33ba6
Source dataset
uspto-grants-2002_12
Patent number
US06492520B1

Reaction notes

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