Nitrogen → HCID 89852321, compound

Participants

Reaction Conditions

Reaction Steps

In a 3 L RBF, a solution of tert-butyl benzyloxycarbamate (Intermediate 153, 86.9 g, 389.22 mmol), N,N(1S,2S)-cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (18.5 g, 23.39 mmol), Pd2(dba)3-CHCl3 (8.05 g, 7.78 mmol) and TBAB (150.5 g, 466.81 mmol) in acetonitrile (1.8 L) was bubbled with N2 for 30 minutes and the flask was closed with a rubber septum. The solution was then kept in a −20° C. freezer for 2 hrs. 2-vinyloxirane (30 g, 428.02 mmol, 1.10 equiv) was added and the mixture was stirred in the freezer (−20-25° C.) for 3 days. The mixture was filtered and the filtrate was evaporated. The residue was purified by silica gel column eluted with EtOAc/hexane (0-40%) to give the title compound (106 g, 93%) as a pale yellow oil.

Provenance & Evidence