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ChemicalBook CAS DataBase List (R)-[1-(4-AMINO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER

(R)-[1-(4-AMINO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER synthesis

3synthesis methods
Carbamic acid, N-[(1S)-1-(4-nitrophenyl)ethyl]-, 1,1-dimethylethyl ester

177947-88-5
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(R)-[1-(4-AMINO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER

255060-77-6
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Yield:255060-77-6 98%

Reaction Conditions:

with iron;ammonium chloride in ethanol;water;Heating / reflux;

Steps:

269.2

To a solution of (S)-tert-butyl 1 -(4-nitrophenyl)ethylcarbamate (9.2 g, 34.6 mmol) in ethanol (184 mL) and water (92 mL) was treated with iron powder (5.5 g, 100 mmol) and ammonium chloride (16.1 g, 303 mmol) and the mixture was refluxed overnight. The reaction was filtered through diatomaceous earth and the filtrate was treated with water and extracted with ethyl acetate. The organics were dried with potassium carbonate filtered and concentrated in vacuo. The resulting oil was dissolved in dichloromethane and passed through a pad of hydrous magnesium silicate and concentrated in vacuo to yield (S)-tert-butyl l-(4-aminophenyl)ethylcarbamate as a yellow oil (8.1 g; 98%; (M+H)-237.2).

References:

WO2008/86462,2008,A2 Location in patent:Page/Page column 126