ChemicalBook CAS DataBase List Carbamic acid, N-[trans-4-(cyanomethyl)cyclohexyl]-, 1,1-dimethylethyl ester

Carbamic acid, N-[trans-4-(cyanomethyl)cyclohexyl]-, 1,1-dimethylethyl ester synthesis

9synthesis methods

Product Name:Carbamic acid, N-[trans-4-(cyanomethyl)cyclohexyl]-, 1,1-dimethylethyl ester
CAS Number:1313279-47-8
Molecular formula:C13H22N2O2
Molecular Weight:238.33

773837-37-9 Synthesis

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((1r,4r)-4-((tert-butoxycarbonyl)amino)cyclohexyl)methyl methanesulfonate

683269-95-6
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$32.00/100mg

Carbamic acid, N-[trans-4-(cyanomethyl)cyclohexyl]-, 1,1-dimethylethyl ester

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Yield: 100%

Reaction Conditions:

in dimethyl sulfoxide at 90; for 4 h;

Steps:

5 Trans (4-Cyanomethyl-cyclohexyl)-carbamic acid tert-butyl ester
A mixture of trans methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohexylmethyl ester (0.93 mg, 3.00 mmol) and sodium cyanide (0.44 g, 9.00 mmol) in DMSO (10 mL) was stirred at 90 °C for 4 hours. After cooling the mixture was partitioned between ethyl acetate and brine and the aqueous phase extracted with ethyl acetate (x2). The combined organic extracts were washed (water and brine), dried (sodium sulfate) and concentrated under vacuum to give 0.72 g (100%) of trans (4-cyanomethyl-cyclohexyl)-carbamic acid tert-butyl ester as a white solid. 1H NMR (400 MHz, CDCI3) δ: 4.38 (br s, 1 H), 3.45-3.33 (m, 1 H), 2.26 (d, 2 H), 2.10-2.02 (m, 2 H), 1.96-1.87 (m, 2 H), 1.71-1.57 (m, 1 H), 1.45 (s, 9 H), 1.26-1.03 (m, 4 H).

References:

F. HOFFMANN-LA ROCHE AG;HURLEY, Christopher;KULAGOWSKI, Janusz;ZAK, Mark WO2013/7768, 2013, A1 Location in patent:Page/Page column 113

773837-37-9 Synthesis

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