benzyl 5-oxo-5,6,7,8-tetrahydronaphthalen-2-ylcarbaMate synthesis

Yield:164149-25-1 93%

Reaction Conditions:

with sodium hydrogencarbonate in tetrahydrofuran at 0 - 20;

Steps:

13.A.1 5-Oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamic acid benzyl ester (Step 1):

To a mixture of 6-amino-3,4-dihydro-2H-naphthalen-1-one (145.0 g, 0.9 mol), NAHCO3 (151.2 g, 1.8 mol) and 1.8 L OF THF at 0 5 C was added benzyl chloroformate (156.7 ML of 97 %, 1.14 mol). The mixture was stirred cold for 2 hours and allowed to stir overnight at room temperature. The solids were filtered off, washed with THF, and the solvent evaporated. The residue was taken up in 1.5 L of ethyl acetate, washed with saturated NAHCO3 and brine, dried over sodium sulfate, filtered, concentrated, and then triturated with heptane to give 248.4 g (93 % yield) of the title compound.

References:

WO2004/69832,2004,A2 Location in patent:Page 115