trans-beta-METHYLSTYRENE → HCID 178455876、化合物

HRID 962300ノート

反応式

HRID 962300 の反応式
C/C=C/c1ccccc1.CC(C)(C)C(=O)ON(Cc1ccccc1)Cc1ccccc1>C1CCOC1.CC(=O)[O-].CC(=O)[O-].CO[Si](C)OC.COc1c(C(C)(C)C)cc(P(c2cc(C(C)(C)C)c(OC)c(C(C)(C)C)c2)c2ccc3c(c2-c2c(P(c4cc(C(C)(C)C)c(OC)c(C(C)(C)C)c4)c4cc(C(C)(C)C)c(OC)c(C(C)(C)C)c4)ccc4c2OCO4)OCO3)cc1C(C)(C)C.[Cu+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1>CC[C@H](c1ccccc1)N(Cc1ccccc1)Cc1ccccc1

参加物

8

反応物 2

HCID 252325trans-beta-METHYLSTYRENEHCID 142744676(Dibenzylamino) 2,2-dimethylpropanoate

生成物 1

HCID 178455876HCID 178455876、化合物収率 86%

試薬・触媒・溶媒 5

HCID 6329250Dimethoxy(methyl)silicon試薬HCID 8895Cupric acetate触媒HCID 11776Triphenylphosphine触媒HCID 111941924,4'-Bi-1,3-benzodioxole-5,5'-diylbis{bis[4-methoxy-3,5-bis(2-methyl-2-propanyl)phenyl]phosphine}触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
23 °C
その他
After dropwise addition of dimethoxy(methyl)- silane into reaction mixture in water bath, the vessel was removed and allowed to stir for an additional 12 hours

後処理

  1. addition手順は記録されていません
  2. addition手順は記録されていません
  3. addition手順は記録されていません
  4. addition手順は記録されていません
  5. extraction3 x 50 mL ethyl acetate extraction · organic 相を保持
  6. concentrationrotary evaporator (35 degC, 50 mmHg)
  7. flash chromatographyThe crude reaction mixture is dissolved in a minimal quantity of benzene or toluene and is loaded onto a column, with interior diameter of roughly 2 inches, packed with silica (200 g, SiliCycle, F60/230-400 mesh) and equilibrated with hexanes. The column is eluted under air pressure with hexanes (500 mL), then 1% ethyl acetate in hexanes (1 L), then 2% ethyl acetate in hexanes (1 L). During elution, fractions are collected in test tubes (roughly 28 mL each), and the desired product typically elutes around fractions 18 through 66. The fractions that contain the productare combined
  8. concentrationrotary evaporator (30 degC, 80 mmHg)

出典と根拠

ORDレコード
ord-7b927700e3414788865b46a4d4b18c44
出典データセット
Copper-Catalyzed Enantioselective Hydroamination of Alkenes
元リンク
出典を表示

反応ノート

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