Lithium Hydroxide → 3-[(tert-Butoxycarbonyl)amino]-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid

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Reaction Steps

(1S,2R,3S,4R)-methyl 3-(tert-butoxycarbonylamino)-7-oxabicyclo[2.2.1]heptane-2-carboxylate (12) (600 mg, 2.2 mmol) was taken in MeOH/H2O (3:1) and LiOH (265 mg, 11 mmol) was added at 0° C. The reaction mixture was allowed to come to rt and then stirred at rt for 16 h. MeOH was removed and saturated ammonium chloride solution was added. This was followed by extraction with DCM. The aqueous extract was acidified to pH 3 using 1N HCl and extracted with DCM again. The combined organic extracts was dried and concentrated to afford the desired product (450 mg, 87%) as an off white solid.

Provenance & Evidence