3-Oxo-Piperidine-1,4-Dicarboxylic Acid 1-Tert-Butyl Ester 4-Ethyl Ester synthesis
- 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
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$13.50/25G
52763-21-0
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71233-25-5
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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
24424-99-5
825 suppliers
$13.50/25G
39514-19-7
139 suppliers
$17.00/1g
71233-25-5
152 suppliers
$6.00/1g
24424-99-5
825 suppliers
$13.50/25G
70637-75-1
38 suppliers
$90.00/50mg
71233-25-5
152 suppliers
$6.00/1g
52763-21-0
242 suppliers
$6.00/1g
71233-25-5
152 suppliers
$6.00/1g
39514-19-7
139 suppliers
$17.00/1g
71233-25-5
152 suppliers
$6.00/1g