1-Piperidinecarboxylic acid, 2-(2-methylpropyl)-4,6-dioxo-, 1,1-dimethylethyl ester synthesis
- Product Name:1-Piperidinecarboxylic acid, 2-(2-methylpropyl)-4,6-dioxo-, 1,1-dimethylethyl ester
- CAS Number:942425-70-9
- Molecular formula:C14H23NO4
- Molecular Weight:269.34
2033-24-1
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Yield:942425-70-9 72%
Reaction Conditions:
with dmap;1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane at 20; for 3 h;
Steps:
2.2
To a stirred solution of 3-(tert-butoxycarbonylamino)-5-methylhexanoic acid (44.0 g, 0.179 mol) in DCM (800 mL) at 0° C., EDC hydrochloride (51.56 g, 0.269 mol), DMAP (32.8 g, 0.269 mol) and Meldrum's acid (25.8 g, 0.179 mol) were added. The reaction mixture was stirred at room temperature for 3 h, washed with 1 N KHSO4 (500 mL), dried over Na2SO4 and concentrated. The residue was dissolved in dry ethyl acetate (1.5 L) and heated under reflux overnight. The reaction mixture was washed with 1 N KHSO4 (500 mL), brine (500 mL), dried over Na2SO4 and concentrated. The residue was purified by column chromatography using petroleum ether and EtOAc (65:35) as eluent to yield 3-(tert-butoxycarbonylamino)-5-methylhexanoic acid as a solid (35 g, 72%).
References:
US2010/261755,2010,A1 Location in patent:Page/Page column 13
3653-34-7
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