3-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester → (3-Methylpyrrolidin-3-yl)(pyrrolidin-1-yl)methanone

HRID 1945496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945496
C(OC([N:8]1[CH2:12][CH2:11][C:10]([CH3:20])([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl.O>[CH3:20][C:10]1([C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[CH2:11][CH2:12][NH:8][CH2:9]1

Komponenten

5

Edukt 1

HCID 596056303-Methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 63140531(3-Methylpyrrolidin-3-yl)(pyrrolidin-1-yl)methanoneAusbeute 79,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 3-methyl-3-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylic acid tert-butyl ester (330 mg, 1.17 mmol) in TFA (5 mL), DCM (5 mL) and water (0.1 mL) was stirred at room temperature for 2 hours and then concentrated under reduced pressure. The residue was taken up in MeOH and loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was washed with MeOH and the desired product was eluted with 2M NH3 in MeOH. The solvents were removed to give (3-Methylpyrrolidin-3-yl)pyrrolidin-1-ylmethanone as a white solid (169 mg, 79%). 1H NMR (400 MHz, CHCl3-d): δ 3.55-3.40 (m, 5 H); 3.06-2.92 (m, 2 H); 2.32-2.20 (m, 2 H); 2.01-1.82 (m, 5 H); 1.71 (m, 1 H); 1.33 (s, 3 H).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. washThe cartridge was washed with MeOH
  3. washthe desired product was eluted with 2M NH3 in MeOH
  4. customThe solvents were removed

Quellen und Nachweise

ORD-Eintrag
ord-5afd057523c6456fbe594783550aed88
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394796B2

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