Ethyl 1-Cbz-5-oxoazepane-4-carboxylate synthesis
- Product Name:Ethyl 1-Cbz-5-oxoazepane-4-carboxylate
- CAS Number:31696-09-0
- Molecular formula:C17H21NO5
- Molecular Weight:319.35
623-73-4
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$26.69/5g
19099-93-5
318 suppliers
$5.00/1g
31696-09-0
61 suppliers
$34.00/250mg
Yield: 88%
Reaction Conditions:
with boron trifluoride diethyl etherate in diethyl ether
Steps:
1 Preparation of 1-benzyl 4-ethyl 5-oxo-1,4-azepanedicarboxylate
PREPARATION 1. Preparation of 1-benzyl 4-ethyl 5-oxo-1,4-azepanedicarboxylate A dry 500 ml 3-neck flask was charged with benzyl 4-oxo-1-piperidinecarboxylate (35.08 g, 150 mmol). It was dissolved in 130 ml Et2O and cooled to -45° C. Ethyldiazoacetate (20.5 ml, 195 mmol) and boron trifluoride ethyl ether (19.4 ml, 158 mmol) were added simultaneously by syringe pump over 45 minutes. The temperature was kept below -25° C. The reaction was stirred for 30 minutes longer, and then quenched with sat. NaHCO3. The ice bath was removed. The reaction was diluted with EtOAc (250 ml) and H2O (150 ml). The layers were separated, and the organic phase was dried over MgSO4. It was concentrated under reduced pressure to an orange oil. The product was purified by flash chromatography (silica gel, 40% EtOAc/hexane), yielding product as pale yellow oil (42.1 g, 88%). 1H NMR (CDCl3) δ 7.39-7.31, 5.15-5.12, 4.42-4.17, 3.96-3.83, 3.75-3.70, 3.65, 3.54-3.37, 2.08-2.03, 1.29-1.24; IR (liq.) 1743, 1702, 1476, 1455, 1443, 1425, 1371, 1318, 1295, 1238, 1213, 1178, 1098, 1068, 1028 cm-1.
References:
Pharmacia & Upjohn Company US6407092, 2002, B1
623-73-4
150 suppliers
$26.69/5g
19099-93-5
318 suppliers
$5.00/1g
31696-09-0
61 suppliers
$34.00/250mg