TERT-BUTYL (5-CYANO-2,3-DIHYDRO-1H-INDEN-1-YL)CARBAMATE synthesis

Yield:903555-96-4 47%

Reaction Conditions:

tetrakis(triphenylphosphine) palladium⁽⁰⁾ in N,N-dimethyl-formamide at 110; for 18 h;

Steps:

D; 1.D

A mixture of (5-bromo-indan-1-yl)-carbamic acid tert-butyl ester (460 mg), Pd(PPh₃)₄ (89 mg), Zn(CN)₂ (200 mg), and DMF (5 mL) under an atmosphere of Ar in a sealed vial was allowed to stir at 110° C. for 18 h. The mixture was allowed to cool to 22° C., Et₂O (20 mL) and water (20 mL) were added. The aqueous layer was washed four times with Et₂O (10 mL). The combined organic layers were washed three times with water (10 mL), once with brine (10 mL), dried over MgSO₄, filtered and concentrated. The resulting residue was purified by silica gel chromatography (4:1 hexanes: ethyl acetate, R_f=0.2) to afford a clear oil (170 mg; 47%). [MH]⁺=259.

References:

US2006/173183,2006,A1 Location in patent:Page/Page column 50-51