1H-Indene-5-carboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-2,3-dihydro-, (1S)- synthesis

Yield:916209-97-7 71%

Reaction Conditions:

Stage #1: C₁₀H₁₁NO₂*ClH;di-tert-butyl dicarbonatewith sodium hydroxide in 1,4-dioxane;water at 20;
Stage #2: with hydrogenchloride in 1,4-dioxane;water;ethyl acetate;

Steps:

9.A

To a solution of the title compound from the Preparative Example 4, Step A (33.7 mg) in l,4-dioxane/H₂O (1:1, 2 mL) were added NaOH (97.4 mg) and di-tert-butyl dicarbonate (68.7 mg). The resulting mixture was stirred at room temperature overnight, diluted with EtOAc, washed with IN aqueous HCl and saturated aqueous NaCl, dried (MgSO₄), and concentrated to give a white solid (34.6 mg, 71%). [MNa]⁺ = 300.

References:

WO2006/128184,2006,A2 Location in patent:Page/Page column 153