Bromobenzene → Methyl 5-oxo-1-phenylprolinate

HRID 534824

반응식

HRID 534824 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[NH:6]1)=[O:4].Br[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:10]=[C:7]1[N:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:9][CH2:8]1

참가 물질

7

반응물 4

HCID 7961BromobenzeneHCID 19660Carbonate IonHCID 500249Methyl 5-oxo-DL-prolinateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

생성물 1

HCID 42260998Methyl 5-oxo-1-phenylprolinate수율 49%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

A mixture of 5-oxo-pyrrolidine-2-carboxylic acid methyl ester (5.00 g, 34.9 mmol), bromobenzene (5.48 g, 34.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.96 g, 1.05 mmol), Xantphos™ (1.21 g, 2.09 mmol), and cecium carbonate (15.9 g, 48.9 mmol) in toluene (100 mL) was stirred at 120° C. for 20 h under argon atmosphere. The reaction mixture was cooled to room temperature, and partitioned between ethyl acetate and 2 M HCl solution. The organic layer was washed with saturated NaHCO3 solution, and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 70:30 to 0:100) to give a yellow solid. The solid was triturated with hexane-diisopropyl ether to give the title compound (3.74 g, 49%) as a yellow solid.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and 2 M HCl solution
  3. washThe organic layer was washed with saturated NaHCO3 solution, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 70:30 to 0:100)
  8. customto give a yellow solid
  9. customThe solid was triturated with hexane-diisopropyl ether

출처 및 근거

ORD 기록
ord-dd26cb1e18be4408962ef6b7a9724af2
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853215B2

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