Lithium Hydroxide → HCID 21548611, compound

HRID 1593651Notes

Reaction equation

HRID 1593651 reaction equation
[F:1][C:2]([F:23])([F:22])[O:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH2:11][CH2:10][CH:9]([C:17]([O:19]CC)=[O:18])[CH2:8][C:7]2=1.[OH-].[Li+]>O1CCCC1.CO>[F:23][C:2]([F:1])([F:22])[O:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]1[CH2:11][CH2:10][CH:9]([C:17]([OH:19])=[O:18])[CH2:8][C:7]2=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69234116HCID 69234116, compound

Product 1

HCID 21548611HCID 21548611, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of ethyl 6-(trifluoromethoxy)-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylate of Step 1 (1.8 g, 5.5 mmol) in tetrahydrofuran (20 mL) and methanol (3 mL) was treated with 1N lithium hydroxide (11 mL) and heated under nitrogen in an oil bath kept at 40° C. for 2 hours. The organic solvents were evaporated, the residue was diluted with water, cooled in an ice bath and acidified with 2N hydrochloric acid (10 mL). The suspension was extracted with ethyl acetate, and the extracts were washed with brine and dried over anhydrous magnesium sulfate. Removal of the solvent provided a colorless foam that was dried in vacuo to yield the title compound (1.6 g). MS [(+)ES, m/z]: 300.1 [M+H]+. MS [(−)ES, m/z]: 298.0 [M−H]−. HPLC: Chromolith Monolith column, 0.46×10 cm, gradient of acetonitrile in water (0.01% TFA), 4 mL/min, detection at 254 nm; Rt 2.0 min.

Workup

  1. temperatureheated under nitrogen in an oil bath
  2. customThe organic solvents were evaporated
  3. additionthe residue was diluted with water
  4. temperaturecooled in an ice bath
  5. extractionThe suspension was extracted with ethyl acetate
  6. washthe extracts were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customRemoval of the solvent
  9. customprovided a colorless foam that
  10. customwas dried in vacuo

Sources & evidence

ORD record
ord-bbd7331878e045468969dbf87920c1c3
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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