Triethylamine → 2,2-dimethyl-3-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid methyl ester

HRID 557701Notes

Reaction equation

HRID 557701 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]([CH3:13])([CH3:12])[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.Cl[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1.C(N(CC)CC)C>O1CCCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]([CH3:12])([CH3:13])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783082-Chloro-5-nitropyridineHCID 592610232,2-Dimethyl-3-(piperidine-4-yl)-propionic acid methyl ester

Product 1

HCID 667381462,2-dimethyl-3-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid methyl esterYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

2,2-Dimethyl-3-(piperidine-4-yl)-propionic acid methyl ester (156 mg, 0.78 mmol) from above was mixed with 2-chloro-5-nitropyridine (124 mg, 0.78 mol) in tetrahydrofuran (2 mL) containing triethylamine (0.24 mL). The mixture was heated in a microwave at 140° C. for 30 minutes. The mixture was extracted with ethyl acetate and water. The organic layer was washed with brine and dried. Solvents were evaporated and the residue was triturated with ether to give 2,2-dimethyl-3-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid methyl ester (199 mg) as a crystalline material. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. extractionThe mixture was extracted with ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. customdried
  4. customSolvents were evaporated
  5. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-7b4d13820e45447984063b330925f50d
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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