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

HRID 1254986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1254986
[CH:1](O)([CH3:3])[CH3:2].[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].C1C[O:25]CC1>>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][C@H:16]([C@@H:19]([OH:25])[CH2:21][O:20][CH:1]([CH3:3])[CH3:2])[CH2:15]1)=[O:13])([CH3:8])([CH3:9])[CH3:10]

Komponenten

5

Edukt 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86650334(S)-(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

Produkt 1

HCID 66859524(S)-3-((R)-1-Hydroxy-2-isopropoxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Isopropyl alcohol (215 μL, 2.8 mmol) was dissolved in THF (428 μL), and the mixture was cooled at 0° C. NaH (33.8 mg, 1.4 mmol) was added in 4 portions, and the mixture stirred for 10 minutes at room temperature. (S)—(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (200 mg, 938 μmol) was added. The resulting solution was placed in a microwave reactor for 10 minutes at 100° C., then cooled to room temperature. The mixture was extracted with Hexanes (10 mL) and washed with 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 give the title compound as a clear oil (162 mg).

Aufarbeitung

  1. waitThe resulting solution was placed in a microwave reactor for 10 minutes at 100° C.
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with Hexanes (10 mL)
  4. washwashed with water (10 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (0-100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-63c8bebabdb14fbca8ce758d378be61a
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455665B2

Notizen zur Reaktion

Wird geladen…