Methanol → [(R)-1-((R)-2-Hydroxy-propyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

HRID 411015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 411015
[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13](=O)[C@H:14]([OH:16])[CH3:15])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].B.CO>C1COCC1>[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][C@H:14]([OH:16])[CH3:15])[CH2:9]1)([CH3:3])([CH3:2])[CH3:4]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 6331BoraneHCID 67334983[(R)-1-((R)-2-Hydroxy-propionyl)-pyrrolidin-3-yl]carbamic acid tert-butyl ester

Produkt 1

HCID 67331578[(R)-1-((R)-2-Hydroxy-propyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl esterAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

[(R)-1-((R)-2-Hydroxy-propyl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (244 mg) was prepared from [(R)-1-((R)-2-hydroxy-propionyl)-pyrrolidin-3-yl]carbamic acid tert-butyl ester (500 mg) and 1 M borane in THF (6 mL). The reaction was stirred at room temperature for 30 min and then stirred at 50° C. for 8 h. The reaction was added to methanol (20 mL). The solvent was evaporated and crude compound was purified by flash chromatography using DCM:methanol gradient.

Aufarbeitung

  1. stirringstirred at 50° C. for 8 h
  2. customThe solvent was evaporated
  3. customcrude compound was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8098f8ef5c0a468bb18064fc7b664856
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759535B2

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