Pyrrolo[3,4-c]pyrrole-2(1H)-carboxylic acid, hexahydro-5-(3-methoxyphenyl)-, 1,1-dimethylethyl ester synthesis

Yield:848592-56-3 97%

Reaction Conditions:

with 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;sodium tertiary butoxide;tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ in toluene at 85; for 18 h;

Steps:

30.A 5-(3-Methoxy-phenyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid Tert-Butyl Ester

EXAMPLE 30A 5-(3-Methoxy-phenyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic Acid Tert-Butyl Ester The product of Example 6C (1.0 g, 4.71 mmol), 3-bromoanisole (1.15 g, 6.12 mmol), tris(dibenzylideneacetone)dipalladium (0) (Pd₂(dba)₃, Strem, 86 mg, 0.094 mmol), racemic-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP, Strem, 0.117 g, 0.188 mmol), and tert-BuONa (0.724 g, 7.54 mmol) were combined in 20 mL toluene. This mixture was warmed to 85° C. and stirred for 18 h then was cooled to ambient temperature, filtered and concentrated under reduced pressure. The crude residue was purified via flash column chromatography (SiO₂, 50% hexanes-EtOAc) to give 1.45 g of the title compound (4.6 mmol, 97% yield). MS (DCI/NH₃) m/z 319 (M+H)⁺.

References:

US2005/65178,2005,A1 Location in patent:Page/Page column 31