Methyl iodide → (S)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidine

HRID 743283노트

반응식

HRID 743283 반응식
[C:1](=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]2[CH:29]=[CH:28][CH:27]=[CH:26][C:18]=2[O:19][CH2:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][NH:22]2)[CH:12]=[CH:13][CH:14]=1.CI>CC(N(C)C)=O.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][C:17]2[CH:29]=[CH:28][CH:27]=[CH:26][C:18]=2[O:19][CH2:20][C@@H:21]2[CH2:25][CH2:24][CH2:23][N:22]2[CH3:1])[CH:12]=[CH:13][CH:14]=1

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 53750852(S)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}pyrrolidine

생성물 1

HCID 10498838(S)-2-{2-[2-(3-Methoxyphenyl)ethyl]phenoxymethyl}-1-methylpyrrolidine수율 104.5%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

130 mg of potassium carbonate were added to a solution of 500 mg of (S)-2-{2-[2-(3-methoxyphenyl)ethyl]phenoxymethyl}pyrrolidine [prepared as described in Example 57(b)] in 5 ml of dimethylacetamide, and the resulting mixture was stirred at room temperature for 5 minutes, after which 288 mg of methyl iodide were added. The reaction mixture was then stirred at room temperature for 5 minutes, after which it was diluted with ethyl acetate. The diluted solution was then washed with water and with a saturated aqueous solution of sodium chloride, in that order, and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of methylene chloride and methanol as the eluent, to give 320 mg (yield 61%) of the title compound as a colorless oil.

후처리

  1. stirringThe reaction mixture was then stirred at room temperature for 5 minutes
  2. washThe diluted solution was then washed with water and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of methylene chloride and methanol as the eluent

출처 및 근거

ORD 기록
ord-32357095520545ca9af602d68b436015
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556864

반응 노트

불러오는 중…