Lithiumtriethylborohydride → 1,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

HRID 132684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132684
C[O:2][C:3](=O)[C@@H:4]1[C@@H:8]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:7][CH2:6][N:5]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C([BH-](CC)CC)C.[Li+]>C1COCC1>[C:20]([O:19][C:17]([N:5]1[CH2:6][CH2:7][C@H:8]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[C@H:4]1[CH2:3][OH:2])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Komponenten

4

Edukt 2

HCID 23664628LithiumtriethylborohydrideHCID 58841066Methyl (2S,3S)-1-Boc-3-[(tert-butyldimethylsilyl)oxy]pyrrolidine-2-carboxylate

Produkt 1

HCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of compound 1H (4.3 g, 12 mmol) in THF (75 mL) at −78° C. under nitrogen was added dropwise 1.0 M lithium triethylborohydride in THF (60 mL, 60 mmol). The reaction was allowed to warm to rt and stirred for 4 h. The reaction was quenched by pouring over ice (150 g) and stirring for 30 min. The product was extracted into EtOAc and washed with saturated aqueous NaHCO3. The organics were dried over MgSO4, filtered and concentrated. Purification by flash chromatography (silica gel, 0-15% EtOAc in hexanes) provided the title compound (3.3 g).

Aufarbeitung

  1. customThe reaction was quenched
  2. additionby pouring over ice (150 g)
  3. stirringstirring for 30 min
  4. extractionThe product was extracted into EtOAc
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialThe organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (silica gel, 0-15% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3835becebbcc42bc819103bf62072944
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388027B2

Notizen zur Reaktion

Wird geladen…