Benzyl Bromide → HCID 86716590, compound

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Reaction Steps

Add benzyl bromide (8.69 mL, 72.9 mmol) dropwise to a stirred suspension of (1S,2S,5R,6R)-2-(tert-butoxycarbonylamino)-4-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (7.27 g, 24.3 mmol) and cesium carbonate (15.83 g, 48.6 mmol) in dry N,N-dimethylformamide (60 mL). Stir the resulting mixture at room temperature overnight under nitrogen. Quench with water and dilute with ethyl acetate. Extract the aqueous phase with ethyl acetate (3 times) and wash the organic layers with brine and water. Dry over sodium sulfate, filter and concentrate to give the crude material as a pale brown oil. Purify by flash chromatography eluting with ethyl acetate:hexane (20:80 to 30:70) to give the title compound as gummy yellow foam (9.15 g, 78.5%). MS (m/z): 502 (M+23).

Provenance & Evidence