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

HRID 268662

반응식

HRID 268662 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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−).

후처리

  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

출처 및 근거

ORD 기록
ord-d6babf1865e744da9febbf66fa31c8f4
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446122B2

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