tert-Butyl 1'-(4-methoxybenzyl)-2'-oxospiro[azetidine-3,3'-indoline]-1-carboxylate synthesis

4synthesis methods

Product Name:tert-Butyl 1'-(4-methoxybenzyl)-2'-oxospiro[azetidine-3,3'-indoline]-1-carboxylate
CAS Number:1603067-25-9
Molecular formula:C23H26N2O4
Molecular Weight:394.46

1-Azetidinecarboxylic acid, 3-[[(2-bromophenyl)[(4-methoxyphenyl)methyl]amino]carbonyl]-, 1,1-dimethylethyl ester

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tert-Butyl 1'-(4-methoxybenzyl)-2'-oxospiro[azetidine-3,3'-indoline]-1-carboxylate

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Yield:1603067-25-9 68.6%

Reaction Conditions:

with [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride;sodium t-butanolate in toluene at 110; for 0.5 h;Microwave irradiation;

Steps:

1.3 tert-butyl 1'-(4-methoxybenzyl)-2'-oxospiro[azetidine-3,3'-indol]-1-carboxylate

The tert-butyl 3-((2-bromophenyl)(4-methoxybenzyl)carbamoyl)azetidine-1-carboxylate(1.63 g, 3.42 _1 ) was dissolved in 5 mL of dry toluene, was added palladium catalyst i-Pr-PEPPSI9 (163 mg, CAS: 905459-27-0), sodium tert-butoxide (493 mg, 5.13 mmol), stirred at 110 ° C microwave for 30 min. The reaction solution was added 100 mL of water, extracted with ethyl acetate (100 mLx2), Merger organic phase was washed with water 100 ml x 3), saturated sodium chloride solution (100 mL x 2), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure, by silica column chromatography eluting with system B agent resulting residue was purified to give tert-butyl 1'-(4-methoxybenzyl)-2'-oxospiro[azetidine-3,3'-indol]-1-carboxylate(3.7g, colorless oil) yield: 68.6%.

References:

TW2016/5834,2016,A Location in patent:Paragraph 0160; 0165; 0166

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References

142253-55-2 Synthesis

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tert-butyl 3-(2-bromophenylcarbamoyl)azetidine-1-carboxylate

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