Trifluoroacetic acid → 2-Benzyloctahydro-4H-isoindol-4-one

HRID 1013426ノート

反応式

HRID 1013426 の反応式
[CH2:1]([N:8]([CH2:14]OC)[CH2:9][Si](C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1(=[O:23])[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]1.C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([N:8]1[CH2:9][CH:22]2[CH:21]([CH2:20][CH2:19][CH2:18][C:17]2=[O:23])[CH2:14]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 135942-Cyclohexen-1-oneHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

生成物 1

HCID 438112032-Benzyloctahydro-4H-isoindol-4-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Benzyl-methoxymethyl-trimethylsilanylmethyl-amine (29.6 g, 0.12 mol) was added to a solution of cyclohex-2-enone (10 g, 0.104 mol) in 500 mL of dichloromethane at 0° C. followed by the dropwise addition of 10 mol % TFA dissolved in 2 mL of dichloromethane. The reaction mixture was stirred at room temperature overnight and was quenched with 50 mL of saturated NaHCO3. The organic layer was washed with 500 mL of brine, dried with MgSO4 and solvent was evaporated in vacuo to give the crude product that was purified by column chromatography (SiO2) using a 2-45% ethylacetate-hexane gradient to afford the subtitle compound. (13.8 g, 60%). MS calculated for C15H19NO +H: 230, observed: 230.

後処理

  1. customwas quenched with 50 mL of saturated NaHCO3
  2. washThe organic layer was washed with 500 mL of brine
  3. dry with materialdried with MgSO4 and solvent
  4. customwas evaporated in vacuo
  5. customto give the crude product that
  6. customwas purified by column chromatography (SiO2)

出典と根拠

ORDレコード
ord-b26f3389de204f5ea1b01e9fffc61bd0
出典データセット
uspto-grants-2011_07
特許番号
US07981919B2

反応ノート

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