Yield:-

Reaction Conditions:

Stage #1: 1-bromo-3-[2-nitroprop-1-enyl]benzenewith lithium aluminium tetrahydride;sulfuric acid in tetrahydrofuran at 0 - 20;
Stage #2: with water;Rochelle's salt at 0;

Steps:

19

[2- (3-Bromo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester: To a stirring solution of lithium aluminum hydride (24 mL of 1 M in tetrahydrofuran (THF), 24 mmol) at 0 °C under an atmosphere of nitrogen was added sulfuric acid (0.61 mL, 12.0 mmol) in tetrahydrofuran (10 mL) dropwise. Then a solution of 1-bromo-3- (2-nitro-propenyl)- benzene (1.17 g, 4.8 mmol) in THF was added dropwise via an addition funnel. Reaction warmed to room temperature overnight. Reaction chilled to 0 °C, and a saturated solution of potassium sodium tartrate tetrahydrate added to the reaction dropwise. Once a cake formed, the organic phase was reduced to an oil under vacuum. This residue was then dissolved in dichloromethane and dried over magnesium sulfate. Di-tert-butyldicarbonate (1.05 g, 4.8 mmol) added and solution stirred overnight at room temperature. Reaction reduced to an oil under vacuum and isolated as a white solid after purification on silica. M+1=314/316.

References:

WO2005/70932,2005,A2 Location in patent:Page/Page column 30-31