Diisopropylethylamine → Ethyl 1-benzyloxymethyl-2-formyl-1H-pyrrol-3-carboxylate

HRID 2097521Notes

Reaction equation

HRID 2097521 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14](Br)=[CH:13][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:11]1[CH:21]=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[H][H]>[Pd].C1(C)C=CC=CC=1>[CH2:1]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:11]1[CH:21]=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 86627040Ethyl 1-benzyloxymethyl-5-bromo-2-formyl-1H-pyrrol-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86627045Ethyl 1-benzyloxymethyl-2-formyl-1H-pyrrol-3-carboxylateYield 103%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

To 43 ml of toluene solution containing 3.66 g (10.0 mmol) of ethyl 1-benzyloxymethyl-5-bromo-2-formyl-1H-pyrrol-3-carboxylate obtained in Reference example 17-(c) were added 2.1 ml of N,N-diisopropylethylamine and 0.4 g of 5% palladium-active carbon, and the mixture was stirred under 1 atm hydrogen atmosphere at room temperature for 6 hours. After completion of the reaction, insoluble material was removed by filtration from the reaction mixture, ethyl acetate was added to the filtrate, and the filtrate was washed successively with water and a saturated aqueous solution of sodium chloride. The organic layer after separation was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 2.96 g the title compound as a pale yellowish solid substantially quantitatively.

Workup

  1. customAfter completion of the reaction, insoluble material
  2. customwas removed by filtration from the reaction mixture, ethyl acetate
  3. additionwas added to the filtrate
  4. washthe filtrate was washed successively with water
  5. customThe organic layer after separation
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6f3cd7db2f1243ceb8c70e9d16887767
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

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