Acetic Acid → (3R,5R)-5-(3-fluorophenyl)pyrrolidin-3-ol

HRID 63985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63985
[Si]([O:8][C@@H:9]1[CH2:13][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[N:11][CH2:10]1)(C(C)(C)C)(C)C.CC(O)=O.[BH4-].[Na+]>CO>[F:20][C:16]1[CH:15]=[C:14]([C@@H:12]2[NH:11][CH2:10][C@H:9]([OH:8])[CH2:13]2)[CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 66847764(R)-3-(tert-butyldimethylsilyloxy)-5-(3-fluorophenyl)-3,4-dihydro-2H-pyrrole

Produkt 1

HCID 67330070(3R,5R)-5-(3-fluorophenyl)pyrrolidin-3-olAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

(R)-3-(tert-butyldimethylsilyloxy)-5-(3-fluorophenyl)-3,4-dihydro-2H-pyrrole (5.0 g, 17.0 mmol) was dissolved in 50 mL methanol and 10 mL AcOH and cooled to −40° C. NaBH4 (1.6 g, 43 mmol) was slowly added in small portions. The reaction was allowed to warm to ambient temperature. Most of the solvent was removed by rotary evaporation. The reaction was taken up in 200 mL of EtOAc, washed with 1 N NaOH, and filtered through Phase Separator filter paper, and concentrated. The crude product was taken up in 20 mL of 2 N HCl in dioxane. The reaction was concentrated, taken up in 200 mL of EtOAc, washed with 1 N NaOH, filtered, and concentrated, yielding the crude product, which was carried to the next step without further purification (2.93 g, 95% yield).

Aufarbeitung

  1. customMost of the solvent was removed by rotary evaporation
  2. washwashed with 1 N NaOH
  3. filtrationfiltered through Phase Separator
  4. filtrationfilter paper
  5. concentrationconcentrated
  6. concentrationThe reaction was concentrated
  7. washwashed with 1 N NaOH
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-be1c1ece2a1a45a8bf1cb39f4cf2d266
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447104B2

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