Dimethyl Sulfide → 2-Cyclopropyl-1-(phenylmethyl)pyrrolidine
Reaktionsgleichung
[CH:1]1([CH:4]2[N:8]([CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7](=O)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.S(C)C>C1COCC1>[CH:1]1([CH:4]2[CH2:5][CH2:6][CH2:7][N:8]2[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:3][CH2:2]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To 5-cyclopropyl-1-(phenylmethyl)-2-pyrrolidinone (240 mg, 1.12 mmol) in THF (5 mL) was added BH3.SMe2 2M in THF (5.6 mL, 11.2 mmol), and the reaction mixture was stirred over the weekend at room temperature. The reaction was quenched with the dropwise addition of CH3OH (˜2 mL, caution: vigorous H2 evolution occurs). The solution was poured onto water (˜50 mL) and EtOAc (˜50 mL), and the mixture was stirred at 60° C. for 3 hours. A saturated aqueous solution of NaHCO3 (˜25 mL) and EtOAc (˜50 mL) were added, and the organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% hexanes to 75% EtOAc/hexanes) afforded the title compound (100 mg, 45%) as a yellow oil. LC-MS (ES) m/z=202 [M+H]+.
Aufarbeitung
- customThe reaction was quenched with the dropwise addition of CH3OH (˜2 mL, caution: vigorous H2 evolution occurs)
- additionThe solution was poured onto water (˜50 mL) and EtOAc (˜50 mL)
- additionA saturated aqueous solution of NaHCO3 (˜25 mL) and EtOAc (˜50 mL) were added
- customthe organic layer was separated
- washwashed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-21ff3720f4dd4107b32cfaec033bea27
- Quelldatensatz
- uspto-grants-2014_04
- Patentnummer
- US08697685B2
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