(Dimethyl sulfide)trihydroboron → HCID 57444163, Verbindung

HRID 44653

Reaktionsgleichung

Reaktionsgleichung von HRID 44653
[ClH:1].[CH3:2][C@:3]([NH2:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=O.CSC.B>C1COCC1>[ClH:1].[ClH:1].[CH3:2][C@:3]([NH2:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][N:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1

Komponenten

4

Edukt 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 57444166(1S)-1-methyl-2-morpholin-4-yl-2-oxo-1-phenylethylamine hydrochloride

Produkt 1

HCID 57444163HCID 57444163, VerbindungAusbeute 0,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under an argon atmosphere 412 mg of (1S)-1-methyl-2-morpholin-4-yl-2-oxo-1-phenylethylamine hydrochloride (1.522 mol) were dissolved in 30 mL of dry THF. A 2 M solution of borane dimethylsulfide (4.4 mL, 5.78 mmol) was added dropwise at 0° C. and the mixture stirred for 10 minutes at 0° C. and then allowed to reach room temperature (gas evolution). After 4 hours the reaction was quenched with methanol (added very carefully) and diluted with methanol when effervescence ceased. THF was removed under vacuo and the methanolic solution was heated at 60° C. for 30 minutes. The solvent was at last completely removed recovering 330 mg of the amine that was subsequently dissolved in 15 mL of dioxane and treated with 1.35 mL of HCl 4 N in dioxane. After 1 hour the solvent was evaporated and the product was triturated with diethylether to yield 350 mg of the expected salt.

Aufarbeitung

  1. customto reach room temperature
  2. customAfter 4 hours the reaction was quenched with methanol (
  3. additionadded very carefully) and
  4. additiondiluted with methanol when effervescence
  5. customTHF was removed under vacuo
  6. temperaturethe methanolic solution was heated at 60° C. for 30 minutes
  7. customcompletely removed
  8. customrecovering 330 mg of the amine that
  9. dissolutionwas subsequently dissolved in 15 mL of dioxane
  10. additiontreated with 1.35 mL of HCl 4 N in dioxane
  11. customAfter 1 hour the solvent was evaporated
  12. customthe product was triturated with diethylether

Quellen und Nachweise

ORD-Eintrag
ord-6dd2cdd212b44c35997c107a4e1b15fb
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541429B2

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