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

HRID 7661

반응식

HRID 7661 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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 5.0 M 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.

후처리

  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)
  6. extractionThe mixture is 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

출처 및 근거

ORD 기록
ord-84b12dc39c894768b6b9c583103a0eff
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087615B2

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