methyl E-4-[5-(3-carboxyprop-1-enyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate → HCID 14882687、化合物

HRID 330208ノート

反応式

HRID 330208 の反応式
[C:1]([CH2:4]/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][CH2:17][CH3:18])[CH:11]=[C:10]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[O:30][CH3:31])([OH:3])=[O:2]>[Pd].C(OCC)(=O)C.O1CCCC1>[C:1]([CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][CH2:17][CH3:18])[CH:11]=[C:10]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[O:30][CH3:31])([OH:3])=[O:2]

参加物

5

反応物 1

HCID 67834906methyl E-4-[5-(3-carboxyprop-1-enyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

生成物 1

HCID 14882687HCID 14882687、化合物収率 80.4%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Palladium on carbon (1.1 g, 10% w/w) was added to a solution of methyl E-4-[5-(3-carboxyprop-1-enyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (10.8 g) in ethyl acetate (300 ml) and tetrahydrofuran (100 ml), and the mixture hydrogenated at atmospheric pressure for 6 hr. The catalyst was removed by filtration through diatomaceous earth, the filter cake washed with ethyl acetate, and the combined filtrate evaporated. The residue was stirred in 1:4 ethyl acetate:hexane (150 ml) and the product isolated by filtration to give methyl 4-[5-(3-carboxypropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (8.72 g, 80%) as an off-white powder; mp 106°-109°; NMR (300 MHz, DMSO-d6): 0.81(t, 3H, CH3), 1.68-1.83(m, 4H), 2.20(t, 2H), 2.61(t, 2H), 3.83(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.02(m, 4H, NCH2, ArCH2Ar'), 6.92(d, 1H), 7.08(s, 1H), 7.23(m, 2H), 7.32(d, 1H), 7.44(m, 2H).

後処理

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washthe filter cake washed with ethyl acetate
  3. customthe combined filtrate evaporated
  4. customhexane (150 ml) and the product isolated by filtration

出典と根拠

ORDレコード
ord-ea6f0aa570da4062979958ce1c67aa88
出典データセット
uspto-grants-1990_01
特許番号
US04894386

反応ノート

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