1-Ethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid → 2-(1-Ethyl-6-isopropyl-8-phenyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-ethanol

HRID 2249542Notes

Reaction equation

HRID 2249542 reaction equation
[CH2:1]([C:3]1([CH2:16][C:17]([OH:19])=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-]>O1CCCC1>[CH2:1]([C:3]1([CH2:16][CH2:17][OH:19])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][C:13]([CH:1]([CH3:3])[CH3:2])=[CH:12][C:11]=3[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 109889991-Ethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 112338272-(1-Ethyl-6-isopropyl-8-phenyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-ethanolYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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-76dbaf62449f417dbd5b922b5761aa97
Source dataset
uspto-grants-2008_01
Patent number
US07314886B2

Reaction notes

Loading…