Trifluoroacetic acid → HCID 57561728, compound

HRID 2069509Notes

Reaction equation

HRID 2069509 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([C:10]([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=O)[CH:9]=1)=[O:4].F[C:18](F)(F)C(O)=O.C([SiH](CC)CC)C>>[CH2:1]([O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([CH2:10][CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:9]=1)=[O:4])[CH3:18]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67487545HCID 67487545, compound

Product 1

HCID 57561728HCID 57561728, compound

Conditions

Temperature
2.5 °C

Procedure

To a mixture of 4-cyclopentanecarbonyl-1H-pyrrole-2-carboxylic acid methyl ester (A1-I) and trifluoroacetic acid was added triethylsilylhydride drop wise under stirring at 0-5° C. Stirring was further continued for 20 hours at 0-25° C. Trifluoroacetic acid was removed under reduced pressure and the residue was diluted with diethyl ether, ether layer was separated and washed with 1N NaOH followed by brine, organic layer was dried over anhydrous sodium sulfate and was evaporated to yield 4-cyclopentylmethyl-1-H-pyrrole-2-carboxylic acid ethyl ester (A1-II).

Workup

  1. stirringStirring
  2. customTrifluoroacetic acid was removed under reduced pressure
  3. additionthe residue was diluted with diethyl ether, ether layer
  4. customwas separated
  5. washwashed with 1N NaOH
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customwas evaporated

Sources & evidence

ORD record
ord-a6f98664e12a4b51b67794c9da9d577a
Source dataset
uspto-grants-2012_10
Patent number
US08299115B2

Reaction notes

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