Water → (5r/s,6r/s)-6-{[(4-Fluorophenyl)sulfanyl]-methyl}spiro[2.4]heptane-5-carboxylic acid

HRID 2222917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2222917
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH:10]2[CH2:16][C:13]3([CH2:15][CH2:14]3)[CH2:12][CH:11]2[C:17]([O:19]CC)=[O:18])=[CH:4][CH:3]=1.COCCOC.[OH-].[Li+].O>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][CH:10]2[CH2:16][C:13]3([CH2:14][CH2:15]3)[CH2:12][CH:11]2[C:17]([OH:19])=[O:18])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 69319826Ethyl(5r/s,6r/s)-6-{[(4 fluorophenyl)sulfanyl]methyl}spiro[2.4]-heptane-5-carboxylate

Produkt 1

HCID 69679911(5r/s,6r/s)-6-{[(4-Fluorophenyl)sulfanyl]-methyl}spiro[2.4]heptane-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl(5R/S,6R/S)-6-{[(4 fluorophenyl)sulfanyl]methyl}spiro[2.4]-heptane-5-carboxylate (66 mg, 0.22 mmol) in 0.3 mL methanol was added ethylene glycol dimethyl ether (1.0 mL) and 2 M aqueous solution of lithium hydroxide (1.0 mL). The reaction mixture was stirred at ambient temperature for 22 h and then poured into 30 mL water. The reaction mixture was washed with 30 mL ether and the aqueous layer was acidified with a 2 M aqueous solution of hydrochloric acid. The product was extracted into ethyl acetate and the combined ethyl acetate extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated to give (5R/S,6R/S)-6-{[(4-fluorophenyl)sulfanyl]-methyl}spiro[2.4]heptane-5-carboxylic acid as a colorless syrup.

Aufarbeitung

  1. washThe reaction mixture was washed with 30 mL ether
  2. extractionThe product was extracted into ethyl acetate
  3. washthe combined ethyl acetate extracts were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-92dc6967655b4193a4fd81f516aab450
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07371747B2

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