4-Methyl-2-oxovaleric acid → 4-Methyl-1-pyrrolidin-1-yl-pentane-1,2-dione

HRID 1446689노트

반응식

HRID 1446689 반응식
[CH3:1][CH:2]([CH3:9])[CH2:3][C:4](=[O:8])[C:5]([OH:7])=O.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1>ClCCl.CN(C)C=O>[CH3:9][CH:2]([CH3:1])[CH2:3][C:4](=[O:8])[C:5]([N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:7]

참가 물질

5

반응물 2

HCID 704-Methyl-2-oxovaleric acidHCID 31268Pyrrolidine

생성물 1

HCID 582867994-Methyl-1-pyrrolidin-1-yl-pentane-1,2-dione수율 66.7%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

Add oxalychloride (5.3 mL, 60.24 mmol, 1.6 eq.) slowly to the solution of 4-methyl-2-oxovaleric acid (4.90 g, 37.65 mmol, 1.0 eq.) in dichloromethane (50 mL) at 0° C. under nitrogen. Add Dimethylforamide (2 drops) last. Stir the reaction mixture overnight. Concentrate in vacuo. Add dichloromethane (100 mL). Add this solution to the solution of pyrrolidine (6.90 g, 97.02 mmol, 2.6 eq.) in dichloromethane (50 mL) at 0° C. slowly under nitrogen. Stir the reaction mixture for 1 hour at room temperature after addition. Wash with HCl (1 N) until the aqueous layer is acidic, then with aqueous saturated sodium chloride (2×20 mL) and water (2×30 mL). Dry the organic phase over MgSO4 and filter the drying reagent off. Concentrate in vacuo. Purify by column chromatography (0%→5% ethyl acetae in dichloromethane) to afford product (4.60 g, 66%).

후처리

  1. concentrationConcentrate in vacuo
  2. stirringStir the reaction mixture for 1 hour at room temperature
  3. additionafter addition
  4. washWash with HCl (1 N) until the aqueous layer
  5. dry with materialDry the organic phase over MgSO4
  6. filtrationfilter the drying reagent off
  7. concentrationConcentrate in vacuo
  8. customPurify by column chromatography (0%→5% ethyl acetae in dichloromethane)

출처 및 근거

ORD 기록
ord-89c8c6e332a74a39a268d03bc922ea35
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666879B2

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