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Ethyl Acetate → (S)-tert-butyl 5,6-dihydroxyhexanoate

HRID 1675997
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1675997
CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=[C:15]([O:22]C)C=C4)N(CC2)C1.[C:59]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])(=[O:65])CCCC=C.CCOC(C)=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].O.[CH2:87]([OH:91])[CH2:88][CH2:89][CH3:90]>>[OH:91][C@H:87]([CH2:15][OH:22])[CH2:88][CH2:89][CH2:90][C:59]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 8857Ethyl AcetateHCID 656671Sodium PyrosulfiteHCID 15047738Tert-butyl hex-5-enoateHCID 22253497Water butanolHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine

Produkt 1

HCID 58209443
(S)-tert-butyl 5,6-dihydroxyhexanoate

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of AD-mix alpha (70 g) in water/butanol 1:1 (512 mL) cooled to 0° C., tert-butyl hex-5-enoate (8.5 g, 49.92 mmol) was added. The reaction mixture was stirred at 4° C. for 70 hrs. Then the reaction mixture was cooled to 0° C. and EtOAc (280 mL), followed by continuous portionwise addition of sodium metabisulfite (20.6 g). The mixture was stirred for 30 min at 0° C. and at rt for 1 hour. The organic layer was separated and the aqueous phase extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluting with EtOAc 100% afforded the title compound as a pale yellow oil.

Aufarbeitung

  1. temperatureThen the reaction mixture was cooled to 0° C.
  2. stirringThe mixture was stirred for 30 min at 0° C. and at rt for 1 hour
  3. customThe organic layer was separated
  4. extractionthe aqueous phase extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-60648327a65642379848fb9f81480c4a
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08003811B2

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