Benzyl Bromide → HCID 86691267, compound

Participants

Reaction Steps

Add cesium carbonate (0.24 g, 730.7 μmol) and benzyl bromide (87.16 μL, 730.7 μmol) to a solution of (1S,2S,5R,6S)-2-(tert-butoxycarbonylamino)spiro[bicyclo[3.1.0]hexane-4,1′-cyclopropane]-2,6-dicarboxylic acid (0.09 g, 292.29 μmol) in N,N-dimethylformamide (2 mL). Stir at room temperature for 1.5 hours under nitrogen. Quench with water and extract with ethyl acetate. Separate the layers and filter the organics through a hydrophobic frit before concentrating to dryness to yield the crude product (134 mg). Purify by flash chromatography eluting with ethyl acetate:iso-hexane (1:99 to 25:75) to give a clear oil. Purify further by flash chromatography eluting with ethyl acetate:iso-hexane (1:99 10:90) to yield the title product (105 mg, 68%) as a clear oil. MS (m/z): 514 (M+23).

Provenance & Evidence