Ethanol → Ethyl-4-(spiro[indene-1,4'-piperidine]-1'-ylmethyl)benzoate

HRID 390392

反応式

HRID 390392 の反応式
Br[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][CH:4]=1.C([N:17]([CH:20]([CH3:22])C)[CH2:18][CH3:19])(C)C.[CH2:23](O)[CH3:24]>>[CH2:10]([O:9][C:7](=[O:8])[C:6]1[CH:12]=[CH:13][C:3]([CH2:2][N:17]2[CH2:18][CH2:19][C:23]3([C:24]4[C:5](=[CH:4][CH:3]=[CH:13][CH:12]=4)[CH:6]=[CH:7]3)[CH2:22][CH2:20]2)=[CH:4][CH:5]=1)[CH3:11]

参加物

4

反応物 3

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 954261Ethyl 4-(bromomethyl)benzoate

生成物 1

HCID 58230576Ethyl-4-(spiro[indene-1,4'-piperidine]-1'-ylmethyl)benzoate収率 60%

反応条件

温度
85 °C

実験手順

To a solution of spiro-[indene-1,4-piperidine]trifluoroacetate (4 g, 14 mmol) in ethanol (25 mL) is added ethyl 4-(bromomethyl)-benzoate (2.9 g, 12.6 mmol), followed by diisopropylethylamine (9.6 mL, 56 mmol). The reaction mixture is refluxed at 85° C. for overnight. The ethanol is removed under reduced pressure and the residue is partitioned between EtOAc (150 mL) and water (50 mL). The organic layer is washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel chromatography, eluting with hexane:ethyl acetate (8.0:2.0) to give the title compound as brown solid (2.8 g, 60%). 1H NMR (400 MHz) 7.94 (d, J=8 Hz, 2H), 7.51 (d, J=8 Hz, 2H), 7.43 (d, J=7.2 Hz, 1H), 7.31 (d, J=7.2 Hz, 1H), 7.18 (m, J=7.2 Hz, 2H), 6.94 (d, J=5.6 Hz, 1H), 6.78 (d, J=5.6 Hz, 1H), 4.30 (q, J=7.2 Hz, 2H), 3.67 (s, 2H), 2.85 (d, J=11.6 Hz, 2H), 2.38 (t, J=11.6 Hz, 2H), 2.09 (t, J=10.4 Hz, 2H), 1.31 (t, J=7.2 Hz, 2H), 1.19 (d, J=12.8 Hz, 2H).

後処理

  1. customThe ethanol is removed under reduced pressure
  2. customthe residue is partitioned between EtOAc (150 mL) and water (50 mL)
  3. washThe organic layer is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with hexane:ethyl acetate (8.0:2.0)

出典と根拠

ORDレコード
ord-6c4aa83c8d2c4cffbab02671451f0b35
出典データセット
uspto-grants-2013_02
特許番号
US08383642B2

関連ノート

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