Tryptophol → (8-Ethyl-1-isopropyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester

HRID 268668

반응식

[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[C:8]2[CH2:12][CH2:13][OH:14])[CH3:2].N1C2C(=CC=CC=2)C(CCO)=C1.[C:27]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])(=O)[CH:28]([CH3:30])[CH3:29]>>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][C:27]1([CH:28]([CH3:30])[CH3:29])[C:9]2[NH:10][C:11]3[C:7]([C:8]=2[CH2:12][CH2:13][O:14]1)=[CH:6][CH:5]=[CH:4][C:3]=3[CH2:1][CH3:2])[CH3:37]

참가 물질

반응물 3

HCID 10685Tryptophol

HCID 81583Ethyl isobutyrylacetate

HCID 1982317-Ethyltryptophol

생성물 1

HCID 69195400(8-Ethyl-1-isopropyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester

실험 절차

Following the procedure of example 22.A. except using 2-(7-ethyl-1H-indol-3-yl)-ethanol as the 3-indolethanol component and ethyl iso-butyrylacetate as ketone component afforded the title compound as a solid. 1H NMR (500 MHz, CDCl3) δ 9.12 (br, 1H), 7.36 (d, 1H), 7.07 (m, 2H), 4.13 (m, 3H), 3.81 (m, 1H), 3.04 (q, 2H), 2.87 (m, 3H), 2.66 (m, 1H), 2.56 (m, 1H), 1.37 (t, 3H), 1.25 (t, 3H), 1.05 (d, 3H), 0.69 (d, 3H).

출처 및 근거

ORD 기록: ord-f04173cf88ac426fb3c81d0208f31c6c
출처 데이터셋: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07446122B2

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