Tryptophol → 8'-Ethyl-4',9'-dihydro-3'H-spiro(cyclohexane-1,1'-pyrano[3,4-b]indole)-4-carboxylic acid ethyl ester

HRID 268670

Reaction equation

[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.[CH2:27]([O:29][C:30]([CH:32]1[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1)=[O:31])[CH3:28]>>[CH2:27]([O:29][C:30]([CH:32]1[CH2:37][CH2:36][C:35]2([C:9]3[NH:10][C:11]4[C:7]([C:8]=3[CH2:12][CH2:13][O:14]2)=[CH:6][CH:5]=[CH:4][C:3]=4[CH2:1][CH3:2])[CH2:34][CH2:33]1)=[O:31])[CH3:28]

Participants

Reactant 3

HCID 10685Tryptophol

HCID 1982317-Ethyltryptophol

HCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 691968928'-Ethyl-4',9'-dihydro-3'H-spiro(cyclohexane-1,1'-pyrano[3,4-b]indole)-4-carboxylic acid ethyl ester

Procedure

Following the procedure of example 24.A. except using 2-(7-ethyl-1H-indol-3-yl)-ethanol as the 3-indolethanol component and 4-oxo-cyclohexane carboxylic acid ethyl ester as ketone component afforded the title compound as an oil. ESI (+) MS m/e=342 (MH+), ESI (−) MS m/e=340 (MH−).

Sources & evidence

ORD record: ord-5b0693fdf6b9439d8229470b8343cdf3
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446122B2

Linked notes

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