(S)-3-aminopiperidin-2-one Hydrochloride synthesis
- Product Name:(S)-3-aminopiperidin-2-one Hydrochloride
- CAS Number:42538-31-8
- Molecular formula:C5H11ClN2O
- Molecular Weight:150.61
3184-13-2
42538-31-8
General procedure for the synthesis of 3-(S)-amino-2-piperidone hydrochloride from L-ornithine hydrochloride: trimethylchlorosilane (2.8 mL, 23 mmol, 4 eq.) was slowly added to L-ornithine hydrochloride (1.0 g, 6.0 mmol, 1 eq.), followed by anhydrous methanol (20 mL). The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solution was cooled to 0 °C and an ethanol solution of 21% (w/w) sodium ethanol (42 mmol, 17 mL) was added dropwise. after 5 min, the reaction system was slowly warmed up to room temperature and stirring was continued for 30 min. The pH of the reaction solution was adjusted with aqueous 6N HCl to 7. The neutralized solution was filtered and the filtrate was concentrated under reduced pressure. The crude product was concentrated again under reduced pressure to remove salts by dissolving in isopropanol and filtering to remove insoluble matter. Finally, the crude product was purified by silica gel fast column chromatography (eluent: 30% methanol/dichloromethane) to afford the target compound 3-(S)-amino-2-piperidone hydrochloride as a hygroscopic light yellow solid.
3184-13-2
652 suppliers
$5.00/250mg
42538-31-8
122 suppliers
$47.00/250mg
Yield: 97%
Reaction Conditions:
Stage #1:L-ornithine hydrochloride with chloro-trimethyl-silane in methanol at 20; under 760.051 Torr; for 12 h;
Stage #2: with sodium ethanolate in methanol;ethanol at 0 - 20; under 760.051 Torr; for 0.583333 h;enantioselective reaction;
Steps:
(S)-3-Aminopiperidin-2-one hydrochloride (4)
Trimethylchlorosilane (2.8 mL, 23 mmol, 4 equiv) was added to L-ornithine·HCl (1.0 g,6.0 mmol, 1 equiv) followed by the addition of anhydrous methanol (20 mL). The mixturestirred at rt for 12 h. The solution was then cooled to 0 °C and a 21% (w/w) solution ofsodium ethoxide in ethanol (42 mmol, 17 mL) was added; after 5 min the solution wasallowed to warm to rt and stirred for another 30 min. The solution was neutralized to pH7 with 6 N aq HCl. The resulting solution was filtered and conc. in vacuo. Salts wereremoved by dissolution in isopropanol, filtered, and conc. in vacuo. The crude residuewas purified by flash column chromatography on silica gel (30% methanol indichloromethane) to afford lactam hydrochloride 4 as a hygroscopic, pale yellow solid.
References:
Barnett, Robert;Raszkowski, Daniel;Winckler, Thomas;Stallforth, Pierre [Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 247 - 250] Location in patent:supporting information
92235-39-7
112 suppliers
$15.00/250mg
42538-31-8
122 suppliers
$47.00/250mg
2480-95-7
6 suppliers
inquiry
42538-31-8
122 suppliers
$47.00/250mg
78397-39-4
13 suppliers
inquiry
42538-31-8
122 suppliers
$47.00/250mg