Sodium methanethiolate → (R)-3-((S)-1-Hydroxy-2-methylsulfanylethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

(R)—(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (1.0 g, 4.7 mmol, 1.0 eq.) in DMF (10 mL) was combined with sodium methyl mercaptide (2.5 g, 14.1 mmol, 3.0 eq.), and the resulting mixture was stirred at 50° C. for 3 hours under nitrogen. Upon completion of the reaction, the mixture was concentrated under vacuum, extracted with EtOAc, washed with saturated aqueous NaCl and water, dried, and concentrated. The crude product was purified by preparative HPLC (MeCN:EtOH=4:6) to yield the title compound (700 mg).

1. customUpon completion of the reaction
2. concentrationthe mixture was concentrated under vacuum
3. extractionextracted with EtOAc
4. washwashed with saturated aqueous NaCl and water
5. customdried
6. concentrationconcentrated
7. customThe crude product was purified by preparative HPLC (MeCN:EtOH=4:6)

ORD-Eintrag

ord-20b679478bd7465790d55aaf28246c49

Quelldatensatz

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08729119B2