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

HRID 268664Notes

Reaction equation

HRID 268664 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

4

Reactant 3

HCID 8028TetrahydrofuranHCID 109889991-Ethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acidHCID 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−).

Workup

  1. customIt was quenched with ethyl acetate carefully
  2. washwashed with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-8678919258e74eb69dd90929952636de
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

Loading…