Water → (S)-3-((R)-1-Hydroxy-2-isopropylsulfanylethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

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Reaktionsgleichung

[CH3:1][CH:2]([SH:4])[CH3:3].[H-].[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][C@H:16]([C@@H:19]2[CH2:21][O:20]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].O>C1COCC1>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][C@H:16]([C@@H:19]([OH:20])[CH2:21][S:4][CH:2]([CH3:3])[CH3:1])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

2-Propanethiol (98.0 μL, 1.1 mmol) was dissolved in THF (250 μL), and the mixture was cooled to 0° C. NaH (12.6 mg, 527 μmol) was slowly added in four portions and the mixture was stirred at room temperature for 10 minutes. (S)—(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (75 mg, 350 μmol) was dissolved in THF (0.1 mL) and added to the mixture. The resulting solution was placed in a microwave reactor for 30 minutes at 100° C., then cooled to room temperature. Hexanes (3×10 mL) was added, followed by water (10 mL). The organic layer was collected, dried over Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography (0-100% EtOAc in hexanes) to yield the title compound as a clear oil (60 mg).

Aufarbeitung

additionadded to the mixture
waitThe resulting solution was placed in a microwave reactor for 30 minutes at 100° C.
temperaturecooled to room temperature
customThe organic layer was collected
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by column chromatography (0-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-4adabddceda24900961475f1bb186628
Quelldatensatz: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08455665B2

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