1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl ester → alpha-[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]-alpha-(thiophene-2-yl)-2-thiophenemethanol

HRID 266103

반응식

HRID 266103 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([C:17]([O:19]C)=O)[CH2:13][CH2:12]2)=[CH:5][CH:4]=1.[Li][C:22]1[S:23][CH:24]=[CH:25][CH:26]=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([C:17]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[OH:19])[CH2:15][CH2:16]2)=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 108695871-[2-(4-Methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl esterHCID 178418439HCID 178418439, 화합물2회

생성물 1

HCID 18930379alpha-[1-[2-(4-Methoxyphenyl)ethyl]-4-piperidinyl]-alpha-(thiophene-2-yl)-2-thiophenemethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

Dissolve 1-[2-(4-methoxyphenyl)ethyl]-4-piperidinecarboxylic acid, methyl ester (4.0 g, 14.42 mmol) in anhydrous tetrahydrofuran (100 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, 2-lithiothiophene (14.42 mL of a 1M solution in tetrahydrofuran, 14.42 mmol) and stir at -78° C. for 3 hours. Add additional 2-lithiothiophene (14.42 mL of a 1M solution in tetrahydrofuran, 14.42 mmol) and stir at -78° C. for 2 hours. Remove the ice bath and allow to warm to room temperature. Quench with saturated ammonium chloride (100 mL), separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (ethyl acetate) and recrystallize (ethyl acetate) to give the title compound as fluffy white crystals; mp 153°-155° C.

후처리

  1. stirringstir at -78° C. for 2 hours
  2. customRemove the ice bath
  3. temperatureto warm to room temperature
  4. customQuench with saturated ammonium chloride (100 mL)
  5. customseparate the organic phase
  6. extractionextract the aqueous phase with ethyl acetate
  7. dry with materialdry (MgSO4)
  8. customevaporate the solvent in vacuo
  9. customPurify by chromatography (ethyl acetate)
  10. customrecrystallize (ethyl acetate)

출처 및 근거

ORD 기록
ord-7218d835a53746d29b2f73d3925084c6
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650416

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