Pyrrolidine → 4-Pyrrolidin-1-yl-pentanoic acid methyl ester

HRID 1695253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695253
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([O:13][CH3:14])(=[O:12])[CH2:7][CH2:8][C:9]([CH3:11])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[CH3:14][O:13][C:6](=[O:12])[CH2:7][CH2:8][CH:9]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:11]

Komponenten

6

Edukt 3

HCID 31268PyrrolidineHCID 69354Methyl levulinateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 671897684-Pyrrolidin-1-yl-pentanoic acid methyl esterAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Pyrrolidine (3 mL, 36 mmol, 1.2 eq) was dissolved in DCM (50 mL) and methyl levulinate (4 mL, 30 mmol, 1.0 eq) was added. The solution was stirred at room temperature for 1 hour, then Na(OAc)3BH (7.6 g, 36.0 mmol, 1.2 eq) was added. The mixture was stirred at room temperature for 16 hours, then brine was added, the crude was extracted with DCM and dried. 2.0 g of the title product were obtained (34% yield).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. extractionthe crude was extracted with DCM
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-b4a98ab8a4ad43019dec2a70013669f0
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163729B2

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