Ethanol → 3',3'-dimethyl-3',4'-dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indole]-8'-carboxylic acid

HRID 853904Notes

Reaction equation

HRID 853904 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:23][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([C:19]([O:21]C)=[O:20])=[CH:11][C:12]=3[C:13]3([O:18][CH2:17][CH2:16][CH2:15][O:14]3)[C:5]2=[N:4][CH2:3]1.CCO.[OH-].[Na+].O>C1COCC1>[CH3:1][C:2]1([CH3:24])[CH2:23][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([C:19]([OH:21])=[O:20])=[CH:11][C:12]=3[C:13]3([O:14][CH2:15][CH2:16][CH2:17][O:18]3)[C:5]2=[N:4][CH2:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 23658058methyl 3',3'-dimethyl-3',4'-dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indole]-8'-carboxylate

Product 1

HCID 116238363',3'-dimethyl-3',4'-dihydro-2'H-spiro[1,3-dioxane-2,10'-pyrimido[1,2-a]indole]-8'-carboxylic acidYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3′,3′-dimethyl-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indole]-8′-carboxylate (0.200 g, 0.610 mmol) in THF (4 mL)/EtOH (4 mL) was added 1N NaOH (2 mL) and H2O (2 mL) and the reaction was refluxed for 1 hr. The reaction was quenched with 1 N HCl and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give the title compound as white solid (0.097 g, 50%). NMR (400 Mz, DMSO-d6): consistent. MS (ES+) m/z 317.3 [M+H]. m.p.: 151.1-153.3° C.

Workup

  1. temperaturethe reaction was refluxed for 1 hr
  2. customThe reaction was quenched with 1 N HCl
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8d54cd68dedb4d2e9123728f2041504c
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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