Water → HCID 59639742, compound

HRID 2249558Notes

Reaction equation

HRID 2249558 reaction equation
[Br:1][C:2]1[C:10]([CH2:11][CH3:12])=[C:9]2[C:5]([C:6]3[CH2:16][CH2:15][O:14][C:13]([CH2:19][C:20]([O:22]CC)=[O:21])([CH2:17][CH3:18])[C:7]=3[NH:8]2)=[CH:4][CH:3]=1.O.[OH-].[Li+].O>O1CCOCC1>[Br:1][C:2]1[C:10]([CH2:11][CH3:12])=[C:9]2[C:5]([C:6]3[CH2:16][CH2:15][O:14][C:13]([CH2:19][C:20]([OH:22])=[O:21])([CH2:17][CH3:18])[C:7]=3[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59639733HCID 59639733, compound

Product 1

HCID 59639742HCID 59639742, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of ethyl 2-(7-bromo-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate (2.8 g, 5 mmol) in dioxane (40 ml) was added lithium hydroxide monohydrate (2.8 g, 67 mmol) and water (30 ml). The mixture was stirred at room temperature overnight. It was concentrated under reduced pressure, neutralized with 5% HCl, extracted with CH2Cl2, dried over MgSO4, and concentrated. The crude product was recrystallized in dichloromethane/hexane (60 ml/20 ml) to give a white solid (980 mg, 53%). 1H NMR (300 MHz, CDCl3) δ 8.68 (br, NH)), 7.27 (d, 1H), 7.19 (d, 1H), 4.06 (m, 2H), 3.04 (qrt, 2H), 2.95 (qrt, 2H), 2.80 (m, 2H), 2.09 (m, 2H), 1.24 (t, 3H), 0.874 (t, 3H).

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was recrystallized in dichloromethane/hexane (60 ml/20 ml)

Sources & evidence

ORD record
ord-46ca6c038a3f4be481a3e953c7392839
Source dataset
uspto-grants-2008_01
Patent number
US07314886B2

Reaction notes

Loading…