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Binap, (A+-)- → 4-(1'-Cyclopropylmethyl-2'-oxo-3,4,5,6,1',2'-hexahydro-2H-[1,4']bipyridinyl-4-yl)-benzoic acid

HRID 2276324
ノート
印刷プレビュー

反応式

HRID 2276324 の反応式
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.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.Br[C:64]1[CH:69]=[CH:68][N:67]([CH2:70][CH:71]2[CH2:73][CH2:72]2)[C:66](=[O:74])[CH:65]=1>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:71]1([CH2:70][N:67]2[CH:68]=[CH:69][C:64]([N:13]3[CH2:14][CH2:15][CH:10]([C:7]4[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:16])=[CH:5][CH:6]=4)[CH2:11][CH2:12]3)=[CH:65][C:66]2=[O:74])[CH2:72][CH2:73]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 634876Binap, (A+-)-HCID 24904226Methyl 4-(piperidin-4-yl)benzoateHCID 585545154-Bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one

生成物 1

HCID 594971014-(1'-Cyclopropylmethyl-2'-oxo-3,4,5,6,1',2'-hexahydro-2H-[1,4']bipyridinyl-4-yl)-benzoic acid

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒
HCID 1140
Toluene
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

4-Piperidin-4-ylbenzoic acid methyl ester (0.40 g, 1.81 mmol), palladium(II) acetate (0.015 g, 0.069 mmol) sodium tert-butoxide (0.34 g, 3.44 mmol) and BINAP (0.06 g, 0.096 mmol) were added to a stirred solution of intermediate D3 (0.31 g, 1.37 mmol) in toluene (10 ml). The reaction mixture was heated at 100° C. for 16 hours in a sealed tube. After cooling to room temperature the mixture was diluted with EtOAc and then filtered through diatomaceous earth, after which the solvent was evaporated in vacuo. The crude residue was treated with a mixture of DCM/methanol and then filtered off. The filtrate was evaporated to dryness in vacuo to yield crude D37 (0.48 g, 100%) that was used without further purification.

後処理

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationfiltered through diatomaceous earth
  3. customafter which the solvent was evaporated in vacuo
  4. additionThe crude residue was treated with a mixture of DCM/methanol
  5. filtrationfiltered off
  6. customThe filtrate was evaporated to dryness in vacuo
  7. customto yield crude D37 (0.48 g, 100%) that
  8. customwas used without further purification

出典と根拠

ORDレコード
ord-6aeb2cab14ec43cdadcf3a56086726e8
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09132122B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート