HCID 68431041, compound → HCID 68430555, compound

HRID 2267156Notes

Reaction equation

HRID 2267156 reaction equation
[C:1]([C:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13](C)([CH3:15])[CH3:14])=[O:11])[CH2:8][CH:9]=1)#[C:2][CH3:3]>Cl>[C:1]([C:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])[CH2:6][CH:5]=1)#[C:2][CH3:3]

Participants

3

Reactant 1

HCID 68431041HCID 68431041, compound

Product 1

HCID 68430555HCID 68430555, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl 4-(1-propynyl)-1,2,3,6-tetrahydropyridine-1-carboxylate (410 mg) prepared in 3) of Example 7 was dissolved in 10% methanolic hydrochloric acid followed by stirring at room temperature for 3 hours and the solvent was evaporated in vacuo. The resulting residue was dissolved in 10 ml of methylene chloride and cooled down to 0° C. and 0.56 ml of triethylamine and 354 mg of isopropyl chloroformate were dropped thereinto. After raising its temperature to room temperature, the reaction was stopped by a saturated aqueous solution of sodium hydrogen carbonate. The product was extracted with ethyl acetate and the organic layer washed with a saturated aqueous solution of ammonium chloride and dried over sodium sulfate. After the solvent was evaporated, the residue was separate and purified by a silica gel column chromatography (hexane/ethyl acetate=4/1) to give 384 mg of a crude product of the title compound.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe resulting residue was dissolved in 10 ml of methylene chloride
  3. temperaturecooled down to 0° C.
  4. addition0.56 ml of triethylamine and 354 mg of isopropyl chloroformate were dropped
  5. temperatureAfter raising its temperature to room temperature
  6. extractionThe product was extracted with ethyl acetate
  7. washthe organic layer washed with a saturated aqueous solution of ammonium chloride
  8. dry with materialdried over sodium sulfate
  9. customAfter the solvent was evaporated
  10. customthe residue was separate
  11. custompurified by a silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-04bcadcdfc9e45f5964f62d763eb98da
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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