Potassium Cyanide → HCID 86751023, compound

Participants

Reaction Steps

A mixture of 90.0 mg (0.147 mmol) of methyl (S)-8-(2-benzyloxycarbonyl-phenoxy)-5-bromo-2-(tert.butoxycarbonylamino)-1,2,3,4-tetrahydro-naphthalene-2-carboxylate, 19.2 mg (0.295 mmol) of potassium cyanide, 6.5 mg (11.8 μmol) of 1,1'-bis-(diphenylphosphino)-ferrocene and 3,0 mg (2.9 μmol) of bis-(dibenzylideneacetone)-di-palladium (Pd2 dba3) in 0.2 ml of N,N-dimethylacetamide was stirred at 800 under argon for 15 hours, cooled and filtered over Celite, whereupon the filtrate was evaporated. The residue was chromatographed on 30 g of silica gel with hexane/ethyl acetate (9:1→1:1), whereby firstly 71 mg (78.9%) of starting material were recovered; subsequently there were obtained about 7.0 mg (8.6%) of crude methyl (S)-8-(2-benzyloxycarbonyl-phenoxy)-2-(tert.butoxycarbonylamino)-5-cyano-1,2,3,4-tetrahydro-naphthalene-2-carboxylate which was purified by means of preparative HPLC chromatography (column: Vydac 250-10 RP-18; programme: 60% acetonitrile→100% acetonitrile in 20 minutes). 5.5 mg (6.7% based on starting material used; 31.6% based on reacted starting product) of pure product were obtained. MS: 556 (M+., <1), 439 (10), 397 (20), 91 (100), 57 (24).

Provenance & Evidence