Triethylamine → HCID 22930059, compound

HRID 1295934Notes

Reaction equation

HRID 1295934 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[CH:12]=[C:11]([C:13](OCC2C=CC=CC=2)=[O:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O.[OH-].[Pd+2].[OH-].[C].CC(C)=O>[CH3:23][N:2]([CH3:1])[C:3]1[CH:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 22929777HCID 22929777, compound

Product 1

HCID 22930059HCID 22930059, compoundYield 92%

Reagents, catalysts & solvents 4

HCID 178502593HCID 178502593, compoundCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

After dissolving 4-benzyl 1-methyl 2-(dimethylamino)terephthalate (1.66 g, 5.3 mmol) in tetrahydrofuran (30 ml), 20% palladium hydroxide-carbon (0.20 g) was added prior to catalytic reduction for 15 minutes at room temperature and normal pressure. The catalyst was separated off, and the solvent was distilled off under reduced pressure to yield a light yellow amorphous substance. This was dissolved in tetrahydrofuran (15 ml), triethylamine (0.81 ml, 5.8 mmol) was added and ethyl chloroformate (0.55 ml, 5.8 mmol) was added dropwise while stirring on ice. After stirring for 30 minutes, the precipitate was filtered off and the filtrate was cooled to −40° C. and stirred. A solution of sodium borohydride (0.44 g, 11.6 mmol) in 5 ml of water was added dropwise, and the temperature of the mixture was gradually increased to −20° C. over a period of 30 minutes. Acetone was added to the reaction mixture, the insoluble portion was filtered off and the solvent was distilled off under reduced pressure. Water was added to the residue and extraction was performed with ethyl acetate. The ethyl acetate layer was washed with water and brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate). The title compound (1.02 g) was obtained as a light yellow oil. (92% yield)

Workup

  1. additionwas added
  2. customThe catalyst was separated off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto yield a light yellow amorphous substance
  5. stirringAfter stirring for 30 minutes
  6. filtrationthe precipitate was filtered off
  7. stirringstirred
  8. temperaturethe temperature of the mixture was gradually increased to −20° C. over a period of 30 minutes
  9. filtrationthe insoluble portion was filtered off
  10. distillationthe solvent was distilled off under reduced pressure
  11. additionWater was added to the residue and extraction
  12. washThe ethyl acetate layer was washed with water and brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. distillationThe solvent was distilled off under reduced pressure
  15. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-38f805aaf1304ea287ec38c9f6e781b1
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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