Tryptophol → 1,3,4,9-Tetrahydro-1-ethyl-pyrano[3,4-b]indole-1-acetic Acid Ethyl Ester

HRID 268662

反応式

HRID 268662 の反応式
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10][CH2:11][OH:12])[C:5]=2[CH:6]=1.[C:13]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=O)[CH2:14][CH3:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][C:13]1([CH2:14][CH3:15])[C:8]2[NH:9][C:4]3[C:5]([C:7]=2[CH2:10][CH2:11][O:12]1)=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH3:22]

参加物

5

反応物 3

HCID 10685TryptopholHCID 78656Ethyl 3-oxovalerateHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 691981331,3,4,9-Tetrahydro-1-ethyl-pyrano[3,4-b]indole-1-acetic Acid Ethyl Ester収率 68%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of tryptophol (1.612 g, 10 mmol), ethyl propionylacetate (1.730 g, 12 mmol), and p-toluenesulfonic acid monohydrate (0.20 g) in benzene (70 mL) was heated to reflux for 5 hours. It was quenched with ethyl acetate and washed with saturated sodium bicarbonate. The organic layer was dried over magnesium sulfate, evaporated to dryness. Flash chromatography on silica gel provided 1.943 g (68%) of the title compound as a solid. mp<80° C. 1H NMR (300 MHz, CDCl3) δ 9.06 (br, 1H), 7.50 (d, 1H), 7.36 (d, 1H), 7.14 (t, 1H), 7.12 (t, 1H), 4.18 (q, 2H), 4.03 (m, 1H), 3.94 (m, 1H), 2.99 (d, 1H), 2.88 (d, 1H), 2.78 (m, 2H), 2.14 (m, 1H), 2.01 (m, 1H), 1.25 (t, 3H), 0.82 (t, 3H); ESI (+) MS m/e=288 (MH+), ESI (−) MS m/e=286 (MH−).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. customIt was quenched with ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-d6babf1865e744da9febbf66fa31c8f4
出典データセット
uspto-grants-2008_11
特許番号
US07446122B2

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