3-(5-Benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester → 3-(5-Hydroxy-indol-1-yl)-3-phenyl-propionic acid ethyl ester

HRID 1295144

반응식

HRID 1295144 반응식
[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[C:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22]CC3C=CC=CC=3)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>[Pd].CO>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([OH:22])=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

참가 물질

4

반응물 1

HCID 674277863-(5-Benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester

생성물 1

HCID 668214783-(5-Hydroxy-indol-1-yl)-3-phenyl-propionic acid ethyl ester수율 96%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A mixture of 3-(5-benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester (1.94 g, 4.89 mmol) and palladium on carbon [10% w/w] (60 mg) in methanol (25 mL) was stirred under hydrogen atmosphere for 24 h. After removal of the catalyst by filtration, the crude product was purified by flash chromatography on silica gel with hexane/ethyl acetate (4:1) to give the title compound in 96% yield. 1H NMR (CDCl3) δ 7.10–7.30 (m, 7H), 6.99 (d, J=2.4 Hz, 1H), 6.69 (dd, J=2.4 and 8.7 Hz, 1H), 6.39 (d, J=3.2 Hz, 1H), 5.99 (t, J=7.6 Hz, 1H), 5.31 (br, 1H), 4.03 (q, J=7.2 Hz, 2H), 3.26 (m, 2H), 1.08 (t, J=7.2 Hz, 3H). 13C NMR (CDCl3) δ 170.4, 149.7, 139.8, 131.5, 129.3, 128.8, 127.9, 126.2, 125.8, 111.6, 110.6, 105.2, 101.4, 61.1, 56.2, 40.4, 13.9. Mass Spectrum (LCMS, ESI) calculated for C19H20NO3 310.1 (M+H); found 310.1.

후처리

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe crude product was purified by flash chromatography on silica gel with hexane/ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-449305433538438f85ec024d6cce68ae
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241789B2

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