Trimethylphosphine → Di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-amino-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate

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Reaction Steps

Add a 1M solution of trimethylphosphine in tetrahydrofuran (19.56 mL, 19.56 mmol) to di-tert-butyl (1S,2R,3R,4S,5R,6S)-4-azido-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]bicyclo[3.1.0]hexane-2,6-dicarboxylate (8.00 g, 13.04 mmol) in tetrahydrofuran (43.46 mL) and water (130.39 mL) at room temperature and stir overnight. Saturated aqueous sodium bicarbonate is added to the reaction then extracted with ethyl acetate (3×). The combined organics are washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure giving the title compound (7.42 g, 12.63 mmol, 97%). MS (m/z): 609/611 (M+Na).

Provenance & Evidence