Methanol → isopropyl 4-[1-phenyl-1H-[1,2,3]-triazol-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylate

HRID 2267171Notes

Reaction equation

HRID 2267171 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([C:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH:17]=3)[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20].CO>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:1]1([N:7]2[CH:11]=[C:10]([C:12]3[CH2:13][CH2:14][N:15]([C:19]([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])[CH2:16][CH:17]=3)[N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 7917Isopropyl chloroformateHCID 197052864-(1-Phenyl-1,2,3-triazol-4-yl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 58945848isopropyl 4-[1-phenyl-1H-[1,2,3]-triazol-4-yl]-1,2,3,6-tetrahydropyridine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

4-[1-phenyl-1H-[1,2,3]triazol-4-yl]-1,2,3,6-tetra-hydropyridine (35 mg) prepared in the above 1) was dissolved in 1 ml of pyridine and 1 ml of chloroform, 32 μl of isopropyl chloroformate was added and the mixture was stirred at room temperature for 1 hour. After an excessive reagent was decomposed by addition of methanol, the reaction solution was concentrated in vacuo and the resulting residue was separated and purified by a preparative thin-layer chromatography (chloroform/methanol 60/1) to give 47 mg of the title compound as a white solid.

Workup

  1. concentrationthe reaction solution was concentrated in vacuo
  2. customthe resulting residue was separated
  3. custompurified by a preparative thin-layer chromatography (chloroform/methanol 60/1)

Sources & evidence

ORD record
ord-320a5c3ce54a48f29b8aed97787b4c46
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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