Dichloromethane → HCID 58945860, compound

HRID 2267148Notes

Reaction equation

HRID 2267148 reaction equation
C(Cl)Cl.[C:4]1(OB(O)O)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:14]1[NH:15][N:16]=[N:17][C:18]=1[C:19]1[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH:24]=1.[OH-].[Na+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C.N1C=CC=CC=1>[C:4]1([N:15]2[N:16]=[N:17][C:18]([C:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:23][CH:24]=3)=[N:14]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 78412Phenyl dihydrogen orthoborateHCID 68430967HCID 68430967, compound

Product 1

HCID 58945860HCID 58945860, compoundYield 10.2%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methylene chloride (2 ml), 60 mg of molecular sieves 4A, 12 mg of phenylboric acid, 8 μl of pyridine and 24 mg of copper(II) acetate were added to 12 mg of tert-butyl 4-(2H-tetrazol-5-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate prepared in 1) and the mixture was stirred at room temperature for 3 hours. After ethyl acetate and a 2N aqueous solution of sodium hydroxide were added thereto, the organic layer washed with a saturated aqueous solution of ammonium chloride and dried over sodium sulfate and the solvent was evaporated in vacuo. The resulting residue was purified by a silica gel thin-layer chromatography (hexane/ethyl acetate=3/1) to give 1.6 mg of the title compound as a crude product.

Workup

  1. customprepared in 1) and the mixture
  2. washthe organic layer washed with a saturated aqueous solution of ammonium chloride
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe resulting residue was purified by a silica gel thin-layer chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-a16bf7b229c94495aacbd2f96547ec34
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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