Piperidine → Benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

HRID 1623665노트

반응식

HRID 1623665 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH2:53]([O:60][C:61]1[CH:76]=[CH:75][C:74](Br)=[CH:73][C:62]=1[C:63]([O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:64])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.[NH:78]1[CH2:83][CH2:82][CH2:81][CH2:80][CH2:79]1>CCOCC.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].C1(C)C=CC=CC=1>[C:54]1([CH2:53][O:60][C:61]2[CH:76]=[CH:75][C:74]([N:78]3[CH2:83][CH2:82][CH2:81][CH2:80][CH2:79]3)=[CH:73][C:62]=2[C:63]([O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)=[O:64])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

참가 물질

8

반응물 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

생성물 1

HCID 66990101Benzyl 2-(benzyloxy)-5-(piperidin-1-yl)benzoate

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

Caesium carbonate (689 mg, 2.11 mmol) was finely ground in a nitrogen-filled glovebox and weighed into an oven-dried Schlenk flask. The flask was quickly capped with a rubber septum and purged with argon. Pd2(dba)3 (3.46 mg, 3.78 μmol) and BINAP (7.05 mg, 0.01 mmol) were added into the flask, followed by benzyl 2-(benzyloxy)-5-bromobenzoate (may be prepared as described in Description 4; 600 mg, 1.51 mmol), piperidine (129 mg, 1.510 mmol), and toluene (10 ml). The solution was refluxed for 10 h. The solution was then cooled to room temperature, diluted with ether, filtered, and concentrated in vacuo to yield the title compound.

후처리

  1. additionfilled glovebox
  2. customweighed into an oven-dried Schlenk flask
  3. customThe flask was quickly capped with a rubber septum
  4. custompurged with argon
  5. temperatureThe solution was refluxed for 10 h
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ed8b03a1c299454fbb1e181f4c9ebc74
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778939B2

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