Triethylamine → (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 856200Notes

Reaction equation

HRID 856200 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][C@:11]([OH:15])([CH3:14])[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.C(N(CC)CC)C.[F:23][C:24]([F:41])([F:40])[C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH2:32][CH2:33][N:34]([C:37](Cl)=[O:38])[CH2:35][CH:36]=2)=[CH:27][CH:26]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:40][C:24]([F:23])([F:41])[C:25]1[CH:26]=[CH:27][C:28]([C:31]2[CH2:36][CH2:35][N:34]([C:37]([O:13][CH2:12][C@@:11]([OH:15])([CH3:14])[CH2:10][N:3]3[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]3[Cl:1])=[O:38])[CH2:33][CH:32]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 16099121(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methylpropane-1,2-diolHCID 230815564-(4-Trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchloride

Product 1

HCID 69479590(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylateYield 31.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(R)-2-Chloro-1-(2,3-dihydroxy-2-methyl)-propyl-4-nitroimidazole prepared in Example 10 (0.74 g, 3.11 mmol) and triethylamine (1.74 ml, 12.42 mmol) were added to a suspension of 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carbonylchloride (0.60 g, 2.07 mmol) in toluene (36 ml) followed by stirring at 100° C. for 16 hours. The mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1) to afford (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine-1-carboxylate (0.32 g, yield 31%) as a light yellow oil.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-0feaa362fe9944058ef8e40f55f2f7b4
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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