Propanal → ((1S,2R)-1-Furan-2-yl-2-methyl-3-oxo-propyl)-carbamic acid tert-butyl ester

HRID 1518746

Reaktionsgleichung

Reaktionsgleichung von HRID 1518746
C1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([O:13][Si](C)(C)C)[C@@H]2CCCN2)C=CC=CC=1.[CH:24](=[O:27])CC.[C:28]([O:32][C:33](=[O:35])[NH2:34])([CH3:31])([CH3:30])[CH3:29]>C(#N)C>[C:28]([O:32][C:33](=[O:35])[NH:34][C@H:21]([C:22]1[O:13][CH:7]=[CH:18][CH:23]=1)[C@@H:20]([CH3:19])[CH:24]=[O:27])([CH3:31])([CH3:30])[CH3:29]

Komponenten

5

Edukt 3

HCID 527PropanalHCID 77922tert-Butyl carbamateHCID 11198150(S)-(-)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol Trimethylsilyl Ether

Produkt 1

HCID 46210818((1S,2R)-1-Furan-2-yl-2-methyl-3-oxo-propyl)-carbamic acid tert-butyl esterAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(diphenyl-trimethylsilanyloxymethyl)-pyrrolidine (417.0 mg, 1.3 mmol, 10 mol %) in acetonitrile (26 mL) at room temperature was added 1-propanal (2.6 mL, 38.4 mmol, 3.0 equiv) and 1-furan-2-yl-meth-(E)-ylidene]-carbamic acid tert-butyl ester (2.5 g, 12.8 mmol). After stirring at room temperature for 12 hours, the reaction mixture was quenched with water (20 mL) and extracted with EtOAc (3×30 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (EtOAc/heptane) to give ((1S,2R)-1-furan-2-yl-2-methyl-3-oxo-propyl)-carbamic acid tert-butyl ester as a light yellow oil (2.4 g, 74% yield, dr=62:38) [dr=62:38 was determined by integration of one set of 1H NMR signal (major s, 9.68 ppm, minor s, 9.76 ppm)]. 1HNMR (400 MHz, CDCl3) 9.76 (s, 1H), 9.68 (s, 1H), 7.34 (d, J=1.57 Hz, 1H), 6.38-6.17 (m, 2H), 5.08 (m, 2H), 2.94 (m, 1H), 1.44 (s, 9H), 1.09 (t, 3H).

Aufarbeitung

  1. customthe reaction mixture was quenched with water (20 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography on silica gel (EtOAc/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-b9993b4b46604f00a4c61bf68dd6c2ad
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09072696B2

Verknüpfte Notizen

Wird geladen…