Carbamic acid, N-(3-formylcyclohexyl)-, 1,1-dimethylethyl ester synthesis
- Product Name:Carbamic acid, N-(3-formylcyclohexyl)-, 1,1-dimethylethyl ester
- CAS Number:1607590-84-0
- Molecular formula:C12H21NO3
- Molecular Weight:227.3
![Carbamic acid, N-[3-[(methoxymethylamino)carbonyl]cyclohexyl]-, 1,1-dimethylethyl ester](/CAS/20210305/GIF/406212-45-1.gif)
406212-45-1
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1607590-84-0
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Yield:1607590-84-0 37%
Reaction Conditions:
with diisobutylaluminium hydride in tetrahydrofuran at -78; for 2 h;
Steps:
32 Synthesis of tert-butyl N-(3-formylcyclohexyl)carbamate:
Into a 1000 mL 3-necked round-botom flask were added tert-butyl N-{3-[methoxy(methyl)carbamoyl]cyclohexyl}carbamate (40.0 g, 139.6 mmol, 1.0 eq) and tetrahydrofuran (0.5 L). After that, to the above mixture was added DIBAL-H (186 mL, 279.2 mmol, 2.0 eq) dropwise at -78°C. The reaction mixture was stirred for an additional 2 hours at -78°C. The resulting mixture was quenched by the addition of sat. NH4CI (aq.) (200 mL) at -78°C and then extracted with ethyl acetate (2x200 mL). The combined organic layers were washed with brine (300 mL), dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under vacuum. The crude residue was purified by a flash column (silica gel, ethyl acetate/petroleum ether =10:1 to 1 :1) to give tert-butyl N-(3- formylcyclohexyl)carbamate (12.0 g, 37%) as colorless oil.
References:
WO2022/159644,2022,A1 Location in patent:Page/Page column 139
334932-13-7
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24424-99-5
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1607590-84-0
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