Water → 4-chloro-5-methyl-N-[(3S,4R)-3-methylpiperidin-4-yl]-1H-pyrrole-2-carboxamide
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][N:14](C(OC)=O)[CH2:13][C@@H:12]2[CH3:21])=[O:9])[NH:5][C:6]=1[CH3:7].[OH-].[K+].O.NN.O>C(O)CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][NH:14][CH2:13][C@@H:12]2[CH3:21])=[O:9])[NH:5][C:6]=1[CH3:7]Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of methyl (3S,4R)-4-{[(4-chloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methylpiperidine-1-carboxylate (Intermediate 38, 2.2 g, 7.05 mmol), potassium hydroxide (2.76 g, 49.35 mmol), and hydrazine hydrate (2.5 mL, 49.35 mmol) in ethylene glycol (150 mL) was stirred for 40 h at 120° C. The reaction mixture was poured in to water (120 mL) and extracted with ethyl acetate (2×150 mL). The combined organic extracts were dried over anhydrous sodium sulphate, filtered, concentrated in vacuo to yield the crude product which was triturated with water (30 mL) to afford 4-chloro-5-methyl-N-[(3S,4R)-3-methylpiperidin-4-yl]-1H-pyrrole-2-carboxamide 950 mg (52%) as brown solid.
Aufarbeitung
- extractionextracted with ethyl acetate (2×150 mL)
- dry with materialThe combined organic extracts were dried over anhydrous sodium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto yield the crude product which
- customwas triturated with water (30 mL)
Quellen und Nachweise
- ORD-Eintrag
- ord-c020c53626204f04a11546943299b23f
- Quelldatensatz
- uspto-grants-2011_12
- Patentnummer
- US08071605B2
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