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

HRID 1096967ノート

反応式

HRID 1096967 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-14867468dabd425a8ecc5798b7e50080
出典データセット
uspto-grants-2012_03
特許番号
US08138197B2

反応ノート

読み込み中…