BENZYL CIS-4-AMINOCYCLOHEXYLCARBAMATE synthesis
- Product Name:BENZYL CIS-4-AMINOCYCLOHEXYLCARBAMATE
- CAS Number:149423-70-1
- Molecular formula:C14H20N2O2
- Molecular Weight:248.32
![Carbamic acid, N-[cis-4-[[(1,1-dimethylethoxy)carbonyl]amino]cyclohexyl]-, phenylmethyl ester](/CAS/20210305/GIF/509143-03-7.gif)
509143-03-7
149423-70-1
Step B: Synthesis of cis-(4-amino-cyclohexyl)-carbamic acid benzyl ester. To a solution of cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester (6.2 g, 0.018 mol) in dichloromethane (40 mL) was added trifluoroacetic acid (2.7 mL, 0.36 mol). The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the excess solvent was removed by rotary evaporation and the resulting oil was dissolved in dichloromethane (30 mL). The organic layer was extracted with dilute aqueous sodium hydroxide/aqueous sodium bicarbonate solution (30 mL). The aqueous layer was back-extracted twice with dichloromethane, and the organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated to give cis-(4-amino-cyclohexyl)-carbamic acid benzyl ester (4.3 g, 97%) as a colorless oil. The product was used directly in the next reaction without further purification.ESI MS m/z 249.2 [M + H]+.
509143-03-7
3 suppliers
inquiry
149423-70-1
55 suppliers
$36.00/1g
Yield: 97%
Reaction Conditions:
with trifluoroacetic acid in dichloromethane at 20; for 4 h;
Steps:
2497.B
Step B: Synthesis of cis-(4-amino-cyclohexyl)-carbamic acid benzyl ester. To a solution of cis-(4-tert-butoxycarbonylamino-cyclohexyl)-carbamic acid benzyl ester (6.2 g, 0.018 mol) in 40 mL CH2Cl2 was added TFA (2.7 mL, 0.36 mol). The solution was stirred at room temperature for 4 hours. The excess solvent was evaporated off and the resulting oil was dissolved in 30 mL CH2Cl2. The organic layer was extracted with 30 mL of a dilute NaOH (aq) / NaHCO3 (aq) solution. The aqueous layer was back extracted twice with CH2Cl2 and the organic layers combined, dried over MgSO4, and concentrated to yield cis-(4-amino-cyclohexyl)-carbamic acid benzyl ester (4.3 g, 97%) as a colorless oil. The oil was carried forward without further purification. ESI MS m/e 249.2 M + H+.
References:
Taisho Pharmaceutical Co. Ltd.;Arena Pharmaceuticals, Inc. EP1464335, 2004, A2 Location in patent:Page/Page column 293
![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
0 suppliers
inquiry
149423-70-1
55 suppliers
$36.00/1g