ChemicalBook CAS DataBase List TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE

TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE synthesis

8synthesis methods

Product Name:TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE
CAS Number:91419-48-6
Molecular formula:C11H20N2O3
Molecular Weight:228.29

84358-13-4

TERT-BUTYL 4-(AMINOCARBONYL)TETRAHYDROPYRIDINE-1(2H)-CARBOXYLATE

91419-48-6

General procedure for the synthesis of tert-butyl 4-carbamoylpiperidine-1-carboxylate from 1-Boc-4-piperidinecarboxylic acid: a mixture of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (220 mg, 2.88 mmol), ammonium chloride (154 mg, 2.88 mmol), EDCI (367 mg, 1.92 mmol) and HOAT (195 mg. 1.44 mmol) were dissolved in dichloromethane (10 mL) at 0 °C, followed by dropwise addition of DIPEA (1.0 mL, 5.77 mmol). After dropwise addition, the reaction mixture was stirred at room temperature for 10 hours. After completion of the reaction, the reaction mixture was washed with distilled water (10 mL x 3). The organic layer was separated and dried with anhydrous Na2SO4 and subsequently concentrated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as eluent to afford tert-butyl 4-carbamoylpiperidine-1-carboxylate as a white solid (160 mg, 73% yield).1H NMR (400 MHz, CD3OD): δ 4.11 (d, J = 13.4 Hz, 2H), 2.76-2.86 (m, 2H), 2.38-2.45 ( m, 1H), 1.79 (d, J = 11.2 Hz, 2H), 1.52-1.62 (m, 2H), 1.47 (s, 9H).MS-ESI: m/z 173.20 [M-55]+.

39546-32-2 Synthesis

39546-32-2
345 suppliers
$6.00/5g

24424-99-5 Synthesis

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

91419-48-6
224 suppliers
$20.80/1G

Yield:91419-48-6 95%

Reaction Conditions:

with 4-methylmorpholine N-oxide in 1,4-dioxane;Product distribution / selectivity;

Steps:

1

The ring nitrogen atom of isonipecotamide 1 (commercially available from Aldrich) was Boc-protected in 95% isolated yield by using Boc20 in dioxane and NMO as the base.

References:

WO2004/2483,2004,A1 Location in patent:Page/Page column 21-22

84358-13-4 Synthesis

84358-13-4
378 suppliers
$5.00/5g

91419-48-6
224 suppliers
$20.80/1G

References

124443-68-1 Synthesis