Acetic Acid → 3-[2-(4-Benzyloxy-phenyl)ethyl]-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

HRID 356524노트

반응식

HRID 356524 반응식
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][CH2:36][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])=[CH:31][CH:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)(=O)C>C1COCC1>[C:17]([O:16][C:13](=[O:15])[CH2:14][C:37]([CH2:36][CH2:35][C:32]1[CH:33]=[CH:34][C:29]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:30][CH:31]=1)([OH:41])[CH:38]([CH3:39])[CH3:40])([CH3:20])([CH3:19])[CH3:18]

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 187986371-(4-(Benzyloxy)phenyl)-4-methylpentan-3-oneHCID 178418339Butyllithium

생성물 1

HCID 539460993-[2-(4-Benzyloxy-phenyl)ethyl]-3-hydroxy-4-methyl-pentanoic acid tert-butyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-40 °C

실험 절차

Diisopropylamine (44.8 mL, 320 mmol) in THF (125 mL) was cooled to -15° C. n-Butyllithium (1.6M, 200 mL, 320 mmol) was added over 20 minutes. The solution was cooled to -40° C. and stirred for 20 minutes. Tert-butyl acetate (43 mL, 320 mmol) in THF (90 mL) was added over 30 minutes and the reaction stirred for 30 minutes at -40° C. 1-(4-Benzyloxy-phenyl)-4-methyl-pentan-3-one (21.0 g, 100 mmol) from Example F in THF (125 mL) was added over 10 minutes and the reaction was stirred at -40° C. for 5 minutes. Acetic acid (40 mL, 700 mmol) was added and the reaction warmed to room temperature. The reaction was stripped to dryness and the product was partitioned between ethyl acetate and saturated NH4Cl. The organic layer was washed with water, 5% NaHCO3 and brine. It was dried (MgSO4) and concentrated to give the title compound.

후처리

  1. additionwas added over 20 minutes
  2. stirringthe reaction stirred for 30 minutes at -40° C
  3. stirringthe reaction was stirred at -40° C. for 5 minutes
  4. temperaturethe reaction warmed to room temperature
  5. customthe product was partitioned between ethyl acetate and saturated NH4Cl
  6. washThe organic layer was washed with water, 5% NaHCO3 and brine
  7. dry with materialIt was dried (MgSO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-83dff350b0ad478abf769e3af813f061
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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