Piperazine → 5,5'-{piperazine-1,4-diylbis[(1S)-1-hydroxyethane-2,1-diyl]}bis(4-methyl-2-benzofuran-1(3H)-one)

HRID 1474358노트

반응식

HRID 1474358 반응식
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C@H:12]1[CH2:14][O:13]1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>CCO>[N:15]1([CH2:14][C@H:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:11])[O:8][CH2:9][C:10]=3[C:2]=2[CH3:1])[OH:13])[CH2:20][CH2:19][N:18]([CH2:14][C@H:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:11])[O:8][CH2:9][C:10]=3[C:2]=2[CH3:1])[OH:13])[CH2:17][CH2:16]1

참가 물질

4

반응물 2

HCID 4837PiperazineHCID 59568665(S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one

생성물 1

HCID 595687025,5'-{piperazine-1,4-diylbis[(1S)-1-hydroxyethane-2,1-diyl]}bis(4-methyl-2-benzofuran-1(3H)-one)

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
150 °C

실험 절차

To a 20 mL microwave tube charged with 4-methyl-5-[(2S)-oxiran-2-yl]-2-benzofuran-1(3H)-one (980 mg, 5.15 mmol) and piperazine (200 mg, 2.3 mmol) was added a stir bar and EtOH (16 mL). The tube was sealed and heated in a microwave apparatus to 150° C. for 90 minutes. The crude product was adsorbed onto silica gel, and purified by flash chromatography (MeOH-DCM 0˜7% gradient). After removal of solvents, 5,5′-{piperazine-1,4-diylbis[(1S)-1-hydroxyethane-2,1-diyl]}bis(4-methyl-2-benzofuran-1(3H)-one) was collected (560 mg).

후처리

  1. additionwas added a stir bar
  2. customThe tube was sealed
  3. custompurified by flash chromatography (MeOH-DCM 0˜7% gradient)
  4. customAfter removal of solvents, 5,5′-{piperazine-1,4-diylbis[(1S)-1-hydroxyethane-2,1-diyl]}bis(4-methyl-2-benzofuran-1(3H)-one)
  5. customwas collected (560 mg)

출처 및 근거

ORD 기록
ord-7d99448b5d524586b039d09d82fa0ec0
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018211B2

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