Water → HCID 59639742, compound

HRID 268681Notes

Reaction equation

HRID 268681 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 59639733Ethyl 2-(7-bromo-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

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-64e8d8332c294ae4a8db23c1b763409e
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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