22540-50-7|6-Oxopiperidine-3-carboxylic acid| Ambeed

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Quality Control of [ 22540-50-7 ] Purity: 98% SDS Specification

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Product Details of [ 22540-50-7 ]

CAS No. :	22540-50-7
Formula :	C₆H₉NO₃
M.W :	143.14
SMILES Code :	OC(=O)C1CCC(=O)NC1
MDL No. :	MFCD08059985
InChI Key :	LWZUSLUUMWDITR-UHFFFAOYSA-N
Pubchem ID :	560090

Safety of [ 22540-50-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 22540-50-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 22540-50-7 ]

[ 22540-50-7 ] Synthesis Path-Downstream 1~20

2
[ 5006-66-6 ]
[ 22540-50-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; sodium hydrogencarbonate; In methanol; water;	EXAMPLE 1 5-Carboxy-2-piperidone To a suspension of 10.0 g of 6-hydroxynicotinic acid in 200 ml water were added 6.5 g of sodium bicarbonate. The resulting solution was subjected to 500 psig hydrogen at 100 C. for 12 hours in the presence of 2.5 g ruthenium on alumina. The catalyst was removed by filtration. The filtrate was acidified to pH 4 with 6N HCl and evaporated to a colorless solid (~15 g). The solid was treated with 40 ml methanol and filtered to remove most of the sodium chloride. The filtrate was evaporated to give 7.5 g of the title compound: MS m/z 143 (M+); 300-MHz 1 H NMR (DMSO-d6) delta1.62-1.77 (m, 1 H), 1.83-1.97 (m, 1 H), 2.00-2.21 (m, 2 H), 2.23-2.35 (m, 1 H), 3.21 (d, J=8 Hz, 2 H), 7, 28 (s, 1 H).

References: [1]Patent: US5159079,1992,A .

3
[ 22540-50-7 ]
[ 146059-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In ethanol;	EXAMPLE 2 5-Ethoxycarbonyl-2-piperidone To a suspension of 250 g of <strong>[22540-50-7]5-carboxy-2-piperidone</strong> in 2.5 liters of punctilious ethanol were added 500 g of thionyl chloride at 22 C. Stir for 18 hours. The resulting solution was evaporated to dryness and the residue triturated with ether to give 233 g of the title compound: MS m/z 171 (M+), 142, 126, 115, 98; 300-MHz 1 H NMR (DMSO-d6) delta1.21 (t, J=7 Hz, 3 H), 1.78-1.92 (m, 1 H), 1.95-2.08 (m, 1 H), 2.15-2.31 (m, 2 H), 2.78-2.89 (m, 1 H), 3.25-3.40 (m, 2 H), 4.12 (t, J=7 Hz, 2 H), 7.95 (s, 1 H).
	With thionyl chloride; In ethanol; at 0 - 20℃; for 24h;	SOCl2 (2.93 g, 24.8 mmol) was dropped into a solution of <strong>[22540-50-7]6-oxopiperidine-3-carboxylic acid</strong> (1,72 g, 12.3 mmol) in (50 mL) at 0 C. Then the reaction was stirred at room temperature for 24 hours.The reaction mixtures was concentratedand the residue was triturated with ether to give white solid. MS (m/z): 172 (M+H)+

References: [1]Patent: US5159079,1992,A .
[2]Patent: WO2014/86032,2014,A1 .Location in patent: Page/Page column 42.

4
[ 1142004-97-4 ]
[ 22540-50-7 ]
[ 1142004-83-8 ]

Yield	Reaction Conditions	Operation in experiment
17%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 120℃; for 4.75h;	To a solution of 6-oxo-piperidine 3-carboxylic acid (0.21 g, 1.5 mmol) in dry DMF (10 ml) was added HBTU (1.13 g, 2.98 mmol), and DIPEA (0.30 g, 0.39 ml, 2.3 mmol) under ice cooled condition, then it was allowed to stir at room temperature for 45 min. To this reaction mixture was added the amine A (0.30 g, 1.5 mmol) in dry DMF dropwise under ice cooled condition. The reaction mixture was then heated for 4 h at 120 C. After the completion of reaction it was cooled, DMF was evaporated completely and then it was dissolved in ethyl acetate (30 ml), and was washed with water (2 x 15 ml), and then with brine, dried (Na2SO4), evaporated under reduced pressure. Final purification was done by column chromatography using flash silica gel (10% methanol/DCM) provided 78 mg (yield: 17%) of the desired product.

References: [1]Patent: WO2009/47359,2009,A1 .Location in patent: Page/Page column 94; 171.

5
[ 71381-75-4 ]
[ 22540-50-7 ]

Yield	Reaction Conditions	Operation in experiment
		Ruthenium(IV) oxide hydrate (1.120 g, 7.41 mmol) and sodium perchlorate (22.70 g, 185 mmol) were stirred in water for 3 min. l-(fert-Butoxycarbonyl)piperidine-3-carboxylic acid (8.50 g, 37.1 mmol) in 15 ml ethyl acetate was added. The mixture was stirred for 3 hr. Then ethyl acetate (50 mL) was added, and the organic layer was separated, washed with brine, dried (MgSO-i), and concentrated under reduced pressure. The resulting residue was stirred in 4 M HC1 (20 mL in dioxane) for 2 hr. Then the volatiles were removed to give Intermediate 6, which was used as is in subsequent reactions. LC-MS: 166.05 [M +Na]+.

References: [1]Patent: WO2011/146354,2011,A1 .Location in patent: Page/Page column 65.

6
C₂₅H₄₄N₄O [ No CAS ]
[ 22540-50-7 ]
[ 1372144-04-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,2-dichloro-ethane;dmap; In dichloromethane; at 20℃; for 5h;	To a solution of intermediate 5b (100 mg, 0.248 mmol) in DCM (5 mL) was added <strong>[22540-50-7]6-oxopiperidine-3-carboxylic acid</strong> (38 mg, 0.265 mmol), EDC (51 mg, 0.266 mmol) and DMAP (2.5 mg) and the solution was stirred at room temperature for 5 h. A second addition of <strong>[22540-50-7]6-oxopiperidine-3-carboxylic acid</strong> (38 mg), EDC (51 mg), and DMAP (2.5 mg) was performed and it was stirred over night. A third addition of <strong>[22540-50-7]6-oxopiperidine-3-carboxylic acid</strong> (38 mg) and EDC (51 mg) was performed and it was stirred over night. The reaction mixture was diluted with DCM (50 mL) and extracted twice with water, saturated sodium bicarbonate solution and with brine. The organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure

References: [1]Patent: EP2439197,2012,A1 .Location in patent: Page/Page column 57.

7
[ 591-50-4 ]
[ 22540-50-7 ]
[ 66608-52-4 ]
[ 123-11-5 ]
C₂₉H₃₁N₃O₄S [ No CAS ]
C₂₉H₃₁N₃O₄S [ No CAS ]