Hydrochloric Acid → 1-Ethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid

HRID 268663Notes

Reaction equation

HRID 268663 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][C:6]1([CH2:19][CH3:20])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[CH:17][CH:16]=[CH:15][CH:14]=3)C.O.[OH-].[Li+].Cl>O1CCOCC1.O>[CH2:19]([C:6]1([CH2:5][C:4]([OH:21])=[O:3])[C:11]2[NH:12][C:13]3[C:18]([C:10]=2[CH2:9][CH2:8][O:7]1)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 691981331,3,4,9-Tetrahydro-1-ethyl-pyrano[3,4-b]indole-1-acetic Acid Ethyl Ester

Product 1

HCID 109889991-Ethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acidYield 42.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (1-ethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester (2.50 g, 8.7 mmol) in 1,4-dioxane was added a solution of lithium hydroxide monohydrate (1.50 g, 35.7 mmol) in water (5 mL). The mixture was stirred at room temperature overnight. It was neutralized with 5% HCl solution and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulfate, and evaporated to dryness. Flash chromatography on silica gel provided 0.954 g (42%) of the title compound as a solid. mp. 135-136° C. 1H NMR (500 MHz, CDCl3) δ 10.0 (br, 1H), 8.55 (br, 1H), 7.51 (d, 1H), 7.34 (d, 1H), 7.18 (t, 1H), 7.12 (t, 1H), 4.12 (m, 1H), 4.06 (m, 1H), 3.01 (d, 1H), 2.99 (d, 1H), 2.85 (m, 2H), 2.10 (m, 1H), 2.03 (m, 1H), 0.86 (t, 3H); ESI (+) MS m/e=260 (MH+), ESI (−) MS m/e=258 (MH−).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-ecd7f10022d24468b53682e4106ac63a
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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