ChemicalBook CAS DataBase List 3-Oxo-Piperidine-1,4-Dicarboxylic Acid 1-Tert-Butyl Ester 4-Ethyl Ester

3-Oxo-Piperidine-1,4-Dicarboxylic Acid 1-Tert-Butyl Ester 4-Ethyl Ester synthesis

5synthesis methods

Product Name:3-Oxo-Piperidine-1,4-Dicarboxylic Acid 1-Tert-Butyl Ester 4-Ethyl Ester
CAS Number:71233-25-5
Molecular formula:C13H21NO5
Molecular Weight:271.31

24424-99-5 Synthesis

24424-99-5
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Ethyl N-benzyl-3-oxo-4-piperidine-carboxylate hydrochloride

52763-21-0
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$6.00/1g

3-Oxo-Piperidine-1,4-Dicarboxylic Acid 1-Tert-Butyl Ester 4-Ethyl Ester

71233-25-5
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$6.00/1g

Yield:71233-25-5 100%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen;sodium carbonate in ethanol at 50; under 28502.9 Torr; for 48 h;Autoclave;

Steps:

64 1-tert-butyl 4-ethyl3-oxopiperidine-1,4-dicarboxylate (74)
1-tert-butyl 4-ethyl3-oxopiperidine-1,4-dicarboxylate (74)
A mixture of ethyl 1-benzyl-3-oxo-4-piperidinecarboxylate hydrochloride (10.0 g,33.58 mmol), Pd/C (10% wt., 1.0 g), Boc20 (14.64g, 67.16 mmol), Na2C03 (3.56 g,33.58 mmol) and EtOH (100 ml)was loaded into a Parr autoclave. Hydrogen was10 introduced (38 bar), and the mixturewas stirred at 50 oc for 48 h. Afterthe autoclave was cooled to 25 oc the hydrogen pressurewas released, the catalyst was removed by filtration, and the mixture was concentrated under reduced pressureto give a yellow oil. Purification by column chromatography (hexane: EtOAc 2:1) gave the title compound(9.10 g, 100%) as a clear oil.15Rf = 0.70 (hexane:EtOAc 2:1); 1H NMR (CDCI3,400 MHz) o 12.10 (s, 1H, enolform -OH),4.25 (q, J= 7.1 Hz, 2H), 4.04 (s, 2H), 3.50 (t, J= 5.8 Hz, 2H), 2.33 (t, J= 5.8 Hz, 2H),1.48 (s, 9H), 1.32 (t, J = 7.1 Hz, 3H); HRMS (CI) calc. for C13H21NOs (M+NH4)+ 289.1763, found: 289.1759.

References:

CANCER RESEARCH TECHNOLOGY LIMITED;IMPERIAL INNOVATIONS LIMITED;BONDKE, Alexander;KROLL, Sebastian;BARRETT, Anthony;FUCHTER, Matthew;SLAFER, Brian;ALI, Simak;COOMBES, Charles;SNYDER, James Patrick WO2015/124941, 2015, A1 Location in patent:Page/Page column 134

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24424-99-5 Synthesis

24424-99-5
867 suppliers
$13.50/25G