4-Methylmorpholine → Tert-butyl 2-[[(4-bromobenzoyl)amino]methyl]pyrrolidine-1-carboxylate

HRID 71720

Reaktionsgleichung

Reaktionsgleichung von HRID 71720
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][NH:14][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][C:16]([Br:15])=[CH:17][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 114644-Bromobenzoic acidHCID 2756484(+-)-2-(Aminomethyl)-1-N-Boc-pyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 58185404Tert-butyl 2-[[(4-bromobenzoyl)amino]methyl]pyrrolidine-1-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.00 g, 4.97 mmol) and 4-bromo-benzoic acid (996 mg, 4.97 mmol) in DMF (25 mL) was added N-methylmorpholine (655 μl, 5.96 mmol) and HATU (1.89 g, 4.97 mmol). After stirring for 3 hours the reaction was concentrated then diluted with EtOAc and washed with 1N HCl, saturated NaHCO3, and brine. The organic phase was then dried over Na2SO4 and concentrated. The crude material was purified by silica gel chromatography (20-50% EtOAc-hexanes gradient) to afford 2-[(4-bromo-benzoylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (1.91 g, 4.97 mmol, quantitative yield). LCMS-ESI+: calc'd for C17H24BrN2O3: 383.1 (M+H+). Found: 383.6 (M+H+).

Aufarbeitung

  1. concentrationwas concentrated
  2. additionthen diluted with EtOAc
  3. washwashed with 1N HCl, saturated NaHCO3, and brine
  4. dry with materialThe organic phase was then dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography (20-50% EtOAc-hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-10725b784f7e497a9e5b5020e59d3d3c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822430B2

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