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

HRID 390392

반응식

HRID 390392 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

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

반응 조건

온도
85 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6c4aa83c8d2c4cffbab02671451f0b35
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383642B2

연결된 노트

불러오는 중…