1-PIPERIDINECARBOXYLIC ACID, 3-(AMINOCARBONYL)-, 1,1-DIMETHYLETHYL ESTER, (3R)- synthesis
- Product Name:1-PIPERIDINECARBOXYLIC ACID, 3-(AMINOCARBONYL)-, 1,1-DIMETHYLETHYL ESTER, (3R)-
- CAS Number:915226-43-6
- Molecular formula:C11H20N2O3
- Molecular Weight:228.29
4138-26-5
24424-99-5
915226-43-6
The general procedure for the synthesis of tert-butyl (R)-3-carbamoylpiperidine-1-carboxylate from 3-piperidinecarboxamide and di-tert-butyl dicarbonate was as follows: to the reaction mixture obtained in Example 4 was added tetrahydrofuran (THF, 40 mL), followed by the addition of di-tert-butyl dicarbonate (37.2 g, 2.3 eq.). The pH of the reaction mixture was adjusted to 10.0 using sodium hydroxide (NaOH). the reaction mixture was stirred at room temperature for 1 hr, after which the precipitated crystals were collected by filtration to afford (R)-1 -(tert-butoxycarbonyl)piperidinamide as white crystals (15.6 g, yield: 93%). The crystals were analyzed using the method described in Example 3; the results showed an optical purity of 99.8% ee. 1H NMR (400 MHz, CDCl3) data were as follows: δ 5.36 (brs, 2H), 3.94-3.08 (m, 5H), 1.96-1.36 (m, 13H).
4138-26-5
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24424-99-5
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915226-43-6
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Yield:915226-43-6 93%
Reaction Conditions:
Stage #1: nipecotamidewith sodium hydroxide at 30; pH=7; for 60 h;Aqueous phosphate buffer;Enzymatic reaction;
Stage #2: di-tert-butyl dicarbonatewith sodium hydroxide in tetrahydrofuran at 20; pH=10; for 1 h;Product distribution / selectivity;
Steps:
5
Example 5Method for producing (R)-1-(tert-butoxycarbonyl)nipecotamide To the reaction mixture obtained in Example 4, THF (40 ml) was added, and di-tert-butyl dicarbonate (37.2 g, 2.3 equivalents) was added thereto. The pH of the reaction mixture was adjusted to 10.0 using NaOH. The reaction mixture was stirred for 1 hour at room temperature, and then the precipitated crystal was filtered off to obtain (R)-1-(tert-butoxycarbonyl)nipecotamide as white crystal (15.6 g, yield: 93%). The crystal was analyzed by the method of Example 3; as a result, the optical purity was 99.8% ee.1H NMR (400 MHz, CDCl3): δ5.36 (brs, 2H), 3.94-3.08 (m, 5H), 1.96-1.36 (m, 13H)
References:
US2010/105917,2010,A1 Location in patent:Page/Page column 16
163438-09-3
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$5.00/250mg
915226-43-6
45 suppliers
$29.00/250mg