Dimethyl Sulfide → 3-(1-Hydroxy-3-methylsulfanylpropyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

HRID 1254997

Reaktionsgleichung

Reaktionsgleichung von HRID 1254997
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:18])[CH2:14][CH2:15][S:16][CH3:17])[C:9]1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]([OH:18])[CH2:14][CH2:15][S:16][CH3:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 1068Dimethyl SulfideHCID 668487143-(3-Methylsulfanylpropionyl)-2-oxo-pyrrolidine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 668597603-(1-Hydroxy-3-methylsulfanylpropyl)pyrrolidine-1-carboxylic Acid t-Butyl EsterAusbeute 166,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3-(3-Methylsulfanylpropionyl)-2-oxo-pyrrolidine-1-carboxylic acid t-butyl ester (188 mg, 654 μmol) was dissolved in THF (531 μL) under nitrogen. 2M BH3.Me2S in THF (981 μL) was added via syringe over 15 minutes. The mixture was stirred at room temperature for 1 hour, then heated at 65° C. for 1 hours, then cooled to room temperature. The mixture was cooled on an ice bath and the reaction was slowly quenched with cold MeOH (100 mL). The mixture was stirred overnight and then diluted with EtOAc (30 mL) and washed with saturated aqueous NaHCO3 (2×50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated by rotary evaporation to yield a yellow oil (300 mg), which was used without further purification. LCMS m/z: [M+H]+ calcd for C13H25NO3S, 275.40. found 276.4.

Aufarbeitung

  1. temperatureheated at 65° C. for 1 hours
  2. temperaturecooled to room temperature
  3. temperatureThe mixture was cooled on an ice bath
  4. customthe reaction was slowly quenched with cold MeOH (100 mL)
  5. stirringThe mixture was stirred overnight
  6. additiondiluted with EtOAc (30 mL)
  7. washwashed with saturated aqueous NaHCO3 (2×50 mL)
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-fc0a24e220a343faa11a238495847265
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455665B2

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