Methyl morpholine oxide → benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate

HRID 906947노트

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HRID 906947 반응식
[OH:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:3]1[CH3:17].C[N+]1([O-])CCOCC1>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:17][C@H:3]1[C:2](=[O:1])[CH2:6][CH2:5][N:4]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

참가 물질

5

반응물 2

HCID 82029Methyl morpholine oxideHCID 59556882benzyl (2S,3S)-3-hydroxy-2-methylpyrrolidine-1-carboxylate

생성물 1

HCID 59556933benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate수율 89%

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

To a solution (150 mL) of benzyl (2S,3S)-3-hydroxy-2-methylpyrrolidine-1-carboxylate (20.5 g) in acetonitrile were added molecular sieves 4A powder (25 g) and 4-methylmorpholine-N-oxide (20.4 g), and the mixture was cooled to 0° C. tetra-n-Propylammonium perruthenate (3.0 g) was added, and the mixture was stirred at 0° C. for 1 hr and at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in ethyl acetate. The insoluble material was filtered through Hyflo Super-Cel. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→2/1) to give the title compound as a colorless oil (yield: 18.0 g, yield: 89%).

후처리

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationThe insoluble material was filtered through Hyflo Super-Cel
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1→2/1)

출처 및 근거

ORD 기록
ord-cd3e8c0fa6454dd3b82ac968c58a9e17
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013008B2

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