Methylparaben → 4-[1-(4-Fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid methyl ester

HRID 889038ノート

反応式

HRID 889038 の反応式
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:23][CH:22]([CH2:24]O)[CH2:21][C:20]2=[O:26])=[CH:15][CH:14]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:24][CH:22]2[CH2:21][C:20](=[O:26])[N:19]([C:16]3[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=3)[CH2:23]2)=[CH:6][CH:5]=1

参加物

7

反応物 5

HCID 7456MethylparabenHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 104656771-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

生成物 1

HCID 117249774-[1-(4-Fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid methyl ester収率 73.1%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

4-Hydroxybenzoic acid methyl ester (0.20 g, 1.314 mmol), 1-(4-fluoro-phenyl)-4-hydroxymethyl-pyrrolidin-2-one (0.33 g, 1.577 mmol), Ph3P (0.345 g, 1.314 mmol) and triethyl amine (0.20 ml, 1.577 mmol) were mixed under argon atmosphere followed by the addition of the dry toluene (10 mL). The reaction mixture was cooled to 0° C. followed by addition of DIAD (0.3 mL, 0.788 mmol) drop wise. The reaction mixture was allowed to warm to room temperature and heated at 80° C. for 24 h. The reaction was quenched with 5% HCl (10 mL), extracted with DCM. The organic layer was dried over Na2SO4 and concentrated to afford the crude product which was purified by flash column chromatography to obtain 4-[1-(4-fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzoic acid methyl ester (0.33 g, 73%) as a white solid.

後処理

  1. temperatureto warm to room temperature
  2. temperatureheated at 80° C. for 24 h
  3. customThe reaction was quenched with 5% HCl (10 mL)
  4. extractionextracted with DCM
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the crude product which
  8. customwas purified by flash column chromatography

出典と根拠

ORDレコード
ord-e188843eb730415bb8a70d76db37aad3
出典データセット
uspto-grants-2012_08
特許番号
US08252797B2

反応ノート

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