Triethylamine → 1-t-Butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 389190ノート

反応式

HRID 389190 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:6]=[C:5]2[O:20][C@H:21]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:23]([C:33]([O:35][CH3:36])=[O:34])[CH2:22]1.[CH:37]([B-](F)(F)F)=[CH2:38].[K+].CCN(CC)CC>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5]([O:20][C@H:21]3[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:23]([C:33]([O:35][CH3:36])=[O:34])[CH2:22]3)=[CH:6][C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:8]2)=[CH:3][C:2]=1[CH:37]=[CH2:38]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 58005143HCID 58005143、化合物

生成物 1

HCID 595711221-t-Butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate収率 95.9%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 702Ethanol溶媒

実験手順

To a solution of the product from Step 5 (14.0 g, 21.5 mmol) in EtOH (300 mL) was added potassium vinyltrifluoroborate (5.05 g, 37.7 mmol), Et3N (5.25 mL, 37.7 mmol) and PdCl2(dppf)-DCM adduct (1025 mg, 1.26 mmol). The reaction mixture was then heated to reflux for 1.5 hours, cooled to RT, concentrated and partitioned between EtOAc and water. The layers were separated and the organic phase dried over Na2SO4, filtered and concentrated. The residue was purified on silica (gradient elution 10% to 80% EtOAc in hexanes) to give the title compound (10.4 g). LRMS (M+H)+ Calcd.: 505.2; found 505.5.

後処理

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 1.5 hours
  3. concentrationconcentrated
  4. custompartitioned between EtOAc and water
  5. customThe layers were separated
  6. dry with materialthe organic phase dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica (gradient elution 10% to 80% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-98d11b6a5bcf4a3ab3c3b013a21e6d86
出典データセット
uspto-grants-2013_02
特許番号
US08377874B2

反応ノート

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