Tetrahydrofuran → (1-Ethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-ethanol

Reaction equation

[CH2:1]([C:3]1([CH2:16][C:17](O)=O)[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:26]1CCCC1>>[CH2:1]([C:3]1([CH:16]([OH:26])[CH3:17])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:2]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 109889991-Ethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid

HCID 21226445Aluminium lithium hydride

Product 1

HCID 69195699(1-Ethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-ethanolYield 79%

Procedure

To solution of (1-ethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid (0.52 g, 2.0 mmol) in tetrahydrofuran (10 mL) was added lithium aluminum hydride (0.114 g, 3.0 mmol) in several small portions. The mixture was stirred at room temperature for 6 hours. It was quenched with ethyl acetate carefully and washed with water. The organic layer was dried over magnesium sulfate and evaporated to dryness. Flash chromatography on silica gel provided 0.389 g (79%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3) δ 7.82 (br, 1H), 7.52 (d, 1H), 7.34 (d, 1H), 7.18 (td, 1H), 7.13 (td, 1H), 4.07 (m, 1H), 4.01 (m, 1H), 3.70 (m, 1H), 3.64 (m, 1H), 2.89 (m, 1H), 2.77 (dt, 1H), 2.71 (br, 1H), 2.20 (m, 1H), 2.05 (m, 1H), 2.00 (m, 1H), 1.90 (m, 1H), 0.94 (t, 3H); ESI (+) MS m/e=246 (MH+), ESI (−) MS m/e=244 (MH−).