Tetrahydrofuran → HCID 58009838, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1S,2R,4R,5R)-7-oxo-3-trimethylsilanyl-6-aza-tricyclo[3.2.1.0(2,4)]octane-6-carboxylic acid tert-butyl ester (1.7 g, 5.7 mmol) and potassium fluoride on alumina (2.10 g, 14.1 mmol) in THF (38 mL) was heated to about 60° C. for about 18 h. The mixture was cooled to ambient temperature and filtered through Celite®. The Celite® pad was rinsed with EtOAc (50 mL) and the filtrate was concentrated under reduced pressure to afford (1R,2S,4R,5R)-4-(tert-butoxycarbonylamino)-6-(trimethylsilyl)bicyclo[3.1.0]hexane-2-carboxylic acid (1.82 g, 100%): LC/MS (Table 2, Method a) Rt=2.62 min; MS m/z: 312 (M−H)−.

Provenance & Evidence