(9-Benzyl-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid → HCID 11349041、化合物

HRID 2249556

反応式

HRID 2249556 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][CH3:18])[C:10]2[CH2:19][CH2:20][O:21][C:22]([CH2:25][C:26](O)=[O:27])([CH2:23][CH3:24])[C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][CH3:18])[C:10]2[CH2:19][CH2:20][O:21][C:22]([CH2:25][CH2:26][OH:27])([CH2:23][CH3:24])[C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

3

反応物 1

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

生成物 1

HCID 11349041HCID 11349041、化合物収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
90 °C

実験手順

To a solution of (9-benzyl-1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid (0.45 g, 1.2 mmol) in tetrahydrofuran at room temperature was added 1.0 M solution of borane-tetrahydrofuran complex in tetrahydrofuran and it was stirred at 90° C. for 4 hours. The mixture was quenched with 5% HCl solution and stirred at room temperature for 20 minutes. It was extracted with ethyl acetate and washed with saturated sodium bicarbonate. The extracts were dried over magnesium sulfate and evaporated to dryness. Flash chromatography on silica gel provided 0.321 g (74%) of the title compound as a solid. 1H NMR (500 MHz, CDCl3) δ 7.17 (m, 3H), 6.94 (d, 1H), 6.84 (m, 2H), 6.70 (t, 1H), 6.56 (d, 1H), 3.87 (m, 1H), 3.79 (m, 1H), 3.68 (dt, 1H), 3.64 (br, 1H), 3.41 (td, 1H), 2.93 (q, 2H), 2.43 (q, 2H), 2.04 (m, 1H), 1.93 (dt, 1H), 1.86 (m, 1H), 1.77 (m, 1H), 1.49 (m, 1H), 1.38 (m, 1H), 1.17 (t, 3H), 0.70 (t, 3H)

後処理

  1. customThe mixture was quenched with 5% HCl solution
  2. stirringstirred at room temperature for 20 minutes
  3. extractionIt was extracted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-3e9256beb3564209abe653bf75c0e1a3
出典データセット
uspto-grants-2008_01
特許番号
US07314886B2

関連ノート

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