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

HRID 1623665ノート

反応式

HRID 1623665 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ed8b03a1c299454fbb1e181f4c9ebc74
出典データセット
uspto-grants-2014_07
特許番号
US08778939B2

反応ノート

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