ChemicalBook CAS DataBase List tert-Butyl 4-(2-oxobenzo[d]oxazol-3(2H)-yl)piperidine-1-carboxylate

tert-Butyl 4-(2-oxobenzo[d]oxazol-3(2H)-yl)piperidine-1-carboxylate synthesis

6synthesis methods

Product Name:tert-Butyl 4-(2-oxobenzo[d]oxazol-3(2H)-yl)piperidine-1-carboxylate
CAS Number:162045-53-6
Molecular formula:C17H22N2O4
Molecular Weight:318.37

79099-07-3 Synthesis

79099-07-3
0 suppliers
$5.00/5g

95-55-6 Synthesis

95-55-6
559 suppliers
$5.00/5G

530-62-1 Synthesis

530-62-1
961 suppliers
$6.00/25g

tert-Butyl 4-(2-oxobenzo[d]oxazol-3(2H)-yl)piperidine-1-carboxylate

162045-53-6
25 suppliers
$291.00/1g

Yield:162045-53-6 38%

Reaction Conditions:

Stage #1: N-tert-butyloxycarbonylpiperidin-4-one;2-amino-phenolwith sodium tris(acetoxy)borohydride in dichloromethane at 20; for 14 h;Inert atmosphere;
Stage #2: 1,1'-carbonyldiimidazole in dichloromethane; for 16 h;

Steps:

1.1 Step 1.1. Synthesis of tert-butyl 4-(2-oxobenzo[d]oxazole-3(2H)-yl)piperidine-l-carboxylate

To a stirred solution of tert-butyl 4-oxy-l-piperidine carboxylate (20g, 100 mmol) and 2-aminophenol (11g, 100 mmol) in CH₂Cl₂ (300 mL), NaBH(OAc)₃ (32.4 g, 151 mmol) was added under nitrogen at room temperature.
The mixture was stirred at room temperature for 14 h, diluted by adding CH₂Cl₂ (1000 mL) and saturated NaHCO₃ (1500 mL), and separated into layers.
The aqueous layer was extracted with CH₂Cl₂ (2* 500ml), the combined organic layer was washed with brine, dried over Na₂SO₄, and the solvent was removed under reduced pressure.
The crude material was diluted with CH₂Cl₂ (300 mL), added with carbonyldiimidazole (18 g, 110 mmol), stirred for 16 h, diluted with CH₂Cl₂ (1 L) and IN HCl (1 L), and separated into layers.
The aqueous layer was extracted with CH₂Cl₂ (2* 500ml), the combined organic layer was washed with brine, dried over Na₂SO₄, and the solvent was removed under reduced pressure.
Purification was performed by silica gel column chromatography (PE: EA = 15:1) to obtain a yellow solid (18.4 g, yield 38%). MS (ESI) m/z 319.0 [M + H]⁺.