Binap, (A+-)- → benzyl (1S,5S)-6-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

Participants

Reaction Steps

The product of Example 52D (451 mg, 1.94 mmol) was coupled with 2,3-dichloro-5-iodopyridine (805 mg, 2.94 mmol; U.S. Pat. No. 7,733,912) using tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 36 mg, 0.039 mmol; Alfa Aesar), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 82 mg, 0.13 mmol; Strem), and sodium tert-butoxide (360 mg, 3.75 mmol; Aldrich) according to the procedure described in Example 1E to provide the title compound (184 mg, 25% yield). MS (DCI/NH3) m/z 378, 380 (M+H)+.

Provenance & Evidence