Diethyl Ether → 2-[2-(4-Fluorophenyl)acetyl]4-methoxy-pyrazolidine-1-carboxylic acid benzyl ester

HRID 7667

반응식

HRID 7667 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[CH3:29]COCC>CN(C)C=O.[Ag]=O>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([O:16][CH3:29])[CH2:13][N:12]1[C:17](=[O:26])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 207247442-[2-(4-Fluorophenyl)acetyl]-4-hydroxypyrazolidine-1-carboxylic acid benzyl ester

생성물 1

HCID 207247452-[2-(4-Fluorophenyl)acetyl]4-methoxy-pyrazolidine-1-carboxylic acid benzyl ester수율 97%

시약·촉매·용매 2

HCID 92152Silver(II) oxide촉매HCID 6228Dimethylformamide용매

실험 절차

2-[2-(4-Fluorophenyl)acetyl]-4-hydroxy-pyrazolidine-1-carboxylic acid benzyl ester, 28, (2.55 g, 7.91 mmol) is dissolved in dimethylformamide (40 mL). Methyl iodide (1.97 mL, 31.6 mmol) is added followed by silver oxide (3.67 g, 15.8 mmol). The flask is cover with foil and stirred overnight in the absence of light. The reaction mixture is poured into ether (150 mL). The mixture is stirred vigorously at room temperature and filtered through a pad of Celite. The filtrate is washed with water (2×150 mL) and brine (150 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford 2.58 g (97% yield) of the desired product as a yellow, clear oil.

후처리

  1. stirringThe mixture is stirred vigorously at room temperature
  2. filtrationfiltered through a pad of Celite
  3. washThe filtrate is washed with water (2×150 mL) and brine (150 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-655bf75cb9f346c6bda87fc87af5a863
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087615B2

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