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

HRID 1922646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922646
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 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, 5H); 3.06-2.92 (m, 2H); 2.32-2.20 (m, 2H); 2.01-1.82 (m, 5H); 1.71 (m, 1H); 1.33 (s, 3H).

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-14a7bde49d4f49c58bb03df3e0d6d50a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

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