Diethyl Ether → 3-methyl 1-(phenylmethyl) 4-[3-chloro-4-(trifluoromethyl)phenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate

HRID 639852ノート

反応式

HRID 639852 の反応式
FC(F)(F)S(O[CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH:8]1[C:23]([O:25][CH3:26])=[O:24])(=O)=O.[Cl:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[C:36]([F:39])([F:38])[F:37].C([O-])([O-])=O.[Na+].[Na+].CCOCC>C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:29][C:30]1[CH:31]=[C:32]([C:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[CH2:9][C:8]=2[C:23]([O:25][CH3:26])=[O:24])[CH:33]=[CH:34][C:35]=1[C:36]([F:37])([F:38])[F:39]

参加物

8

反応物 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 37729583-Chloro-4-(trifluoromethyl)benzeneboronic acidHCID 866201973-Methyl 1-(phenylmethyl) 4-{[(trifluoromethyl)sulfonyl]oxy}-1,3-piperidinedicarboxylate

生成物 1

HCID 592560273-methyl 1-(phenylmethyl) 4-[3-chloro-4-(trifluoromethyl)phenyl]-5,6-dihydro-1,3(2H)-pyridinedicarboxylate収率 94.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 3-methyl 1-(phenylmethyl) 4-{[(trifluoromethyl)sulfonyl]oxy}-1,3-piperidinedicarboxylate (3 g) (P38) and [3-chloro-4-(trifluoromethyl)phenyl]boronic acid (1.826 g) in dry toluene (37 mL) under N2 atmosphere at 0° C., Pd(PPh3)4 (292 mg) dissolved in absolute EtOH (26 ml), was added followed by Na2CO3 2M (21 mL). The reaction mixture was heated to 80° C. for 2 h. Et2O was then added to the solution and the organic phase was separated. The aqueous layer was extracted with Et2O and the combined organic phases were washed with saturated NaCl aqueous solution, dried and concentrated under vacuum. The crude was purified by flash-chromatography (eluting with cyclohexane/ethyl acetate from 9:1 to 8:2) to give the title compound (3.03 g).

後処理

  1. additionwas added
  2. customthe organic phase was separated
  3. extractionThe aqueous layer was extracted with Et2O
  4. washthe combined organic phases were washed with saturated NaCl aqueous solution
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe crude was purified by flash-chromatography (eluting with cyclohexane/ethyl acetate from 9:1 to 8:2)

出典と根拠

ORDレコード
ord-8d03fd01c2df4146a943d123b6f4b349
出典データセット
uspto-grants-2010_04
特許番号
US07691893B2

反応ノート

読み込み中…