Pyrrolidine → Methyl 3-{[ethoxymethyl]tetrazol-5-yl}-5-pyrrolidin-1-ylbenzoate

HRID 1096967Notes

Reaction equation

HRID 1096967 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].FC(F)(F)S(O[C:20]1[CH:21]=[C:22]([CH:27]=[C:28]([C:30]2[N:34]([CH2:35][O:36][CH2:37][CH2:38][Si](C)(C)C)[N:33]=[N:32][N:31]=2)[CH:29]=1)[C:23]([O:25][CH3:26])=[O:24])(=O)=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[CH2:37]([O:36][CH2:35][N:34]1[C:30]([C:28]2[CH:27]=[C:22]([CH:21]=[C:20]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])=[N:31][N:32]=[N:33]1)[CH3:38]

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 62657Potassium Phosphate, TribasicHCID 86635509Methyl 3-{[(trifluoromethyl)-sulfonyl]oxy}-5-[({[2-(trimethylsilyl)ethyl]oxy}methyl)tetrazol-5-yl]benzoate

Product 1

HCID 66782512Methyl 3-{[ethoxymethyl]tetrazol-5-yl}-5-pyrrolidin-1-ylbenzoate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

Pyrrolidine (41 mg), Pd2(dba)3 (35 mg), tBu2-P-Ph-Ph (23 mg) and potassium phosphate (241 mg) were added in that order to a DME (5 mL) solution of methyl 3-{[(trifluoromethyl)-sulfonyl]oxy}-5-[({[2-(trimethylsilyl)ethyl]oxy}methyl)tetrazol-5-yl]benzoate (183 mg), and stirred at 85° C. for 4 hours. The reaction liquid was filtered through Celite, the solvent was evaporated away, the residue was diluted with ethyl acetate, water was added thereto, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated saline water, dried with anhydrous sodium sulfate, filtered, and the solvent was evaporated away. The residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a red oil.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. customthe solvent was evaporated away
  4. additionthe residue was diluted with ethyl acetate, water
  5. additionwas added
  6. extractionthe solution was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated saline water
  8. dry with materialdried with anhydrous sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was evaporated away
  11. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-14867468dabd425a8ecc5798b7e50080
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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