4-Nitrobenzyl bromide → HCID 57565267、化合物

HRID 2110129ノート

反応式

HRID 2110129 の反応式
[C:1]1([C:10]([OH:12])=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)([O-:15])=[O:14].N12CCCN=C1CCCCC2>C(O)C.C1C=CC=CC=1.[Pd]>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][O:11][C:10]([CH:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[O:12])=[CH:18][CH:17]=1)([O-:15])=[O:14]

参加物

7

反応物 3

HCID 660114-Nitrobenzyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 842611H-indene-3-carboxylic acid

生成物 1

HCID 57565267HCID 57565267、化合物収率 95%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 241Benzene溶媒HCID 702Ethanol溶媒

実験手順

To a solution of 3H-Indene-1-carboxylic acid (2.0 g, 13.3 mmol) in ethanol (35 mL) was added 10% Pd/C (200 mg). The reaction mixture was stirred under an H2 atmosphere for 1 h. The mixture was filtered through Celite and concentrated in vacuo. The residue was combined with p-nitrobenzyl bromide (5.8 g, 26.8 mmoles) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.4 mL, 16.0 mmol) in 65 mL of benzene, and was stirred at 50° C. for 20 hours. After this period the heterogeneous mixture was gravity filtered and the filtrate was evaporated in vacuo. The residue was combined with CH2Cl2 and was washed with 1N HCl (2×25 mL) and sat'd NaHCO3 (2×25 mL), and the resulting CH2Cl2 solution was dried over anhydrous Na2SO4. The crude solid was purified using flash silica chromatography (0-10% EtOAc/Hexane) to yield 3.61 g (95%) of the intermediate.

後処理

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. stirringwas stirred at 50° C. for 20 hours
  4. waitAfter this period the heterogeneous mixture was
  5. filtrationgravity filtered
  6. customthe filtrate was evaporated in vacuo
  7. washwas washed with 1N HCl (2×25 mL) and sat'd NaHCO3 (2×25 mL)
  8. dry with materialthe resulting CH2Cl2 solution was dried over anhydrous Na2SO4
  9. customThe crude solid was purified

出典と根拠

ORDレコード
ord-571a85624402413697954cf93a787410
出典データセット
uspto-grants-2009_04
特許番号
US07517884B2

反応ノート

読み込み中…