Etodolac → (9-Benzyl-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid

HRID 268678

反応式

HRID 268678 の反応式
[CH2:1]([C:3]1([CH2:18][C:19]([OH:21])=[O:20])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:16][CH3:17])[CH3:2].[H-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[CH2:24]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][CH3:17])[C:7]2[CH2:6][CH2:5][O:4][C:3]([CH2:18][C:19]([OH:21])=[O:20])([CH2:1][CH3:2])[C:8]1=2)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 3308EtodolacHCID 7498Benzyl BromideHCID 24758Sodium hydride

生成物 1

HCID 69196678(9-Benzyl-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid (0.51 g, 1.8 mmol) in tetrahydrofuran at room temperature was added sodium hydride (60% dispersion in mineral oil, 0.4 g). After being heated at 50° C. for 2 hours, benzyl bromide (0.6 g, 3.5 mmol) was added and the solution was stirred for another 2 hours. It was quenched with ethyl acetate and washed with water. The ethyl acetate layer was dried over magnesium sulfate and evaporated to dryness. Flash chromatography on silica gel provided 0.486 g (73%) of the title compound as a solid. 1H NMR (500 MHz, CDCl3) δ 7.13 (m, 3H), 6.97 (d, 1H), 6.74 (d, 1H), 6.68 (t, 1H), 6.21 (d, 1H), 3.90 (s, 1H), 3.63 (m, 1H), 3.35 (td, 1H), 3.18 (d, 1H), 3.00 (d, 1H), 2.67 (q, 2H), 2.44 (q, 2H), 2.10 (m, 1H), 1.85 (d, 1H), 1.52 (m, 1H), 1.41 (m, 1H), 1.16 (t, 3H), 0.75 (t, 3H); ESI (+) MS m/e=278 (MH+).

後処理

  1. customIt was quenched with ethyl acetate
  2. washwashed with water
  3. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-ba82f5d35b844a3f8283f864b64f66fb
出典データセット
uspto-grants-2008_11
特許番号
US07446122B2

関連ノート

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