Pyridine → HCID 13560806, compound

HRID 1285553Notes

Reaction equation

HRID 1285553 reaction equation
C1C=C[NH+]=CC=1.Br[Br-]Br.[CH3:10][C:11]1[NH:12][C:13]([CH3:37])=[C:14]([C:30]([O:32]C(C)(C)C)=[O:31])[CH:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].N1C=CC=CC=1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[CH3:10][C:11]1[NH:12][C:13]2[CH2:37][O:32][C:30](=[O:31])[C:14]=2[CH:15]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:16]=1[C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18]

Participants

5

Reactant 2

HCID 1049PyridineHCID 1116134HCID 1116134, compound

Product 1

HCID 13560806HCID 13560806, compoundYield 29.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a manner similar to that previously described, 1.14 gram of 80 percent pyridinium bromide perbromide (2.85 millimoles) was added to a cooled to 0° C. solution of 1.00 gram (2.59 millimoles) of di-t-butyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate and 0.81 milliliter of pyridine in 20 milliliters of dry chloroform. The resulting mixture was stirred for 30 minutes at 0° C. and then heated at reflux for 90 minutes. Thereafter, the mixture was cooled to room temperature, diluted with 200 milliliters of ethyl acetate and washed successively with 5 percent hydrochloric acid and brine, dried over magnesium sulfate, then filtered to remove the drying agent and the filtrate subjected to reduced pressure to vaporize the solvent and recover 0.90 gram of product as a yellow oil. The oil was chromatographed on 50 grams of silica gel using 1:1 ethyl acetate-hexane as eluant to obtain 250 milligrams (29 percent yield) of white crystalline t-butyl 2-methyl-4 -phenyl-5-oxo-1,4,5,7-tetrahydrofuro[3,4-b]pyridine-3-carboxylate product which after recrystallization from diethyl ether and drying at 70° C./0.05 millimeters Hg pressure for 48 hours and 100° C./0.005 millimeters Hg for 24 hours had a melting point of 185°-188° C. Elemental analyses for the product were as follows:

Workup

  1. temperatureheated
  2. temperatureat reflux for 90 minutes
  3. temperatureThereafter, the mixture was cooled to room temperature
  4. washwashed successively with 5 percent hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customto remove the drying agent
  8. customrecover 0.90 gram of product as a yellow oil
  9. customThe oil was chromatographed on 50 grams of silica gel using 1:1 ethyl acetate-hexane as eluant

Sources & evidence

ORD record
ord-97b0d3db28fa4547bf218a550e3b4ecc
Source dataset
uspto-grants-1986_01
Patent number
US04567268

Reaction notes

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