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

HRID 22687

反応式

HRID 22687 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O: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.CCOCC>C1COCC1>[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

参加物

4

反応物 2

HCID 3283Diethyl EtherHCID 129701552-[2-(4-Fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester

生成物 1

HCID 207247442-[2-(4-Fluorophenyl)acetyl]-4-hydroxypyrazolidine-1-carboxylic acid benzyl ester収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2-[2-(4-Fluorophenyl)acetyl]-4-oxo-pyrazolidine-1-carboxylic acid benzyl ester, 11, (1.0 g, 2.81 mmol) is dissolved in THF (30 mL) and the solution cooled to −78° C. A S 5.0M solution of borane-dimethyl sulfide complex in ether (1.2 mL, 5.61 mmol) is added dropwise. After 1 hour at −78° C., the reaction is quenched by slow addition of NH4Cl (sat. aq.) (10 mL). The cooling bath is then removed, and the mixture allowed to warm to room temperature with vigorous stirring. The THF is removed in vacuo and the residue diluted with water (50 mL) The mixture is extracted with ethyl acetate (2×100 mL), dried, filtered and concentrated in vacuo to give a yellow oil which is purified over silica (1:1 to 1:2 hexane/ethyl acetate to 100% ethyl acetate) to afford 731 mg (73% yield) as a clear, viscous oil.

後処理

  1. customthe reaction is quenched by slow addition of NH4Cl (sat. aq.) (10 mL)
  2. customThe cooling bath is then removed
  3. temperatureto warm to room temperature with vigorous stirring
  4. customThe THF is removed in vacuo
  5. additionthe residue diluted with water (50 mL) The mixture
  6. extractionis extracted with ethyl acetate (2×100 mL)
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a yellow oil which
  11. customis purified over silica (1:1 to 1:2 hexane/ethyl acetate to 100% ethyl acetate)
  12. customto afford 731 mg (73% yield) as a clear, viscous oil

出典と根拠

ORDレコード
ord-77142665f35e4ece862b4b5a4a34dd90
出典データセット
uspto-grants-2005_02
特許番号
US06849627B2

関連ノート

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