Triphenylphosphine → 1-Methyl-2-{2-[2-(4-phenylbutyl)phenoxy]ethyl}pyrrolidine

HRID 743178

反応式

HRID 743178 の反応式
N(C(OCC)=O)=NC(OCC)=O.[C:13]1([CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O[CH2:31][CH2:32][CH:33]1[CH2:37][CH2:36][CH2:35][N:34]1[CH3:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:38][N:34]1[CH2:35][CH2:36][CH2:37][CH:33]1[CH2:32][CH2:31][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][CH2:21][CH2:20][CH2:19][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 933631-Methyl-2-pyrrolidineethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 125964892-(4-Phenylbutyl)phenol

生成物 1

HCID 106907751-Methyl-2-{2-[2-(4-phenylbutyl)phenoxy]ethyl}pyrrolidine収率 38.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

522 mg of diethyl azodicarboxylate were added, whilst ice-cooling and stirring, to a solution of 226 mg of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3), 390 mg of 2-(2-hydroxyethyl)-1-methylpyrrolidine and 790 mg of triphenylphosphine in 40 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 14 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The resulting yellow oily concentrate was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 130 mg (yield 38%) of the title compound as an oil.

後処理

  1. temperaturecooling
  2. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  3. customthe resulting residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. concentrationThe resulting yellow oily concentrate
  8. customwas purified by column chromatography through silica gel
  9. additionby volume mixture of methylene chloride and methanol as the eluent

出典と根拠

ORDレコード
ord-44ff11fcdf43427b82b5b5b4d26b3704
出典データセット
uspto-grants-1996_09
特許番号
US05556864

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