ChemicalBook CAS DataBase List tert-Butyl 3-oxo-4-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate

tert-Butyl 3-oxo-4-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate synthesis

3synthesis methods

Product Name:tert-Butyl 3-oxo-4-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate
CAS Number:647863-25-0
Molecular formula:C12H16F3NO4
Molecular Weight:295.25

383-63-1 Synthesis

383-63-1
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$10.00/25g

98977-36-7 Synthesis

98977-36-7
429 suppliers
$6.00/1g

tert-Butyl 3-oxo-4-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate

647863-25-0
35 suppliers
$290.00/250mg

Yield:647863-25-0 81%

Reaction Conditions:

Stage #1: 3-oxo-piperidine-1-carboxylic acid tert-butyl esterwith lithium hexamethyldisilazane in tetrahydrofuran;1,2-dimethoxyethane at -78; for 1 h;Cooling with acetone-dry ice;
Stage #2: ethyl trifluoroacetate, in tetrahydrofuran;1,2-dimethoxyethane at -78 - 20; for 3.5 h;

Steps:

3.a; 47

5.0 g (25 mmol) of t-butyl 3-oxpiperidin-l -carboxylate was dissolved in dimethoxyethane, and the resulting solution was cooled to -78°C, then 30 mL (30 mmol) of lithium hexamethyldisilazane (LHMDS, IM in THF) was dropwise added and stirred for about 1 hour, followed by dropwise addition of 3.9 mL (33 mmol) of ethyltrifluoroacetate. After stirring for 1 hour, a dryice/acetone bath was removed and then further stirred for about 2 hours and 30 minutes with the reaction solution being heated to room temperature. After the reaction solution was washed with a saturated aqueous ammonium chloride, extraction was conduced three times with ethyl acetate. An organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, then the residue was purified by column chromatography (20:1 dichloromethane:methanol) to give 6.0 g of the title compound in a yield of 81%.[831] ¹K NMR (CDCl₃) δ 4.22 (2H, br s), 3.56 (2H, m), 2.57 (2H, br s), 1.49 (9H, s)[832] Mass (m/e) 296 (M+l)

References:

WO2006/104356,2006,A1 Location in patent:Page/Page column 18; 61

98977-36-7 Synthesis

98977-36-7
429 suppliers
$6.00/1g

647863-25-0
35 suppliers
$290.00/250mg

References

1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-5-[(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester

647863-23-8
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1(2H)-Pyridinecarboxylic acid, 5,6-dihydro-3-[(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester

647863-24-9
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407-25-0 Synthesis

407-25-0
437 suppliers
$9.00/1g

647863-25-0
35 suppliers
$290.00/250mg

1-Piperidinecarboxylic acid, 3-oxo-2-(2,2,2-trifluoroacetyl)-, 1,1-dimethylethyl ester

647863-26-1
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References