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

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Reaction Steps

Potassium carbonate (5.11 g, 36.60 mmol) is added to a solution of di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-[(tert-butoxycarbonyl)amino]-3-[(3,4-dichlorobenzyl)oxy]-4-{[(4-nitrophenyl)carbonyl]oxy}bicyclo[3.1.0]hexane-2,6-dicarboxylate (9.00 g, 12.20 mmol) and methanol (122.01 mL, 3.01 moles), and then stirred at room temperature. After 1 hour, dilute the reaction mixture with ethyl acetate, wash with water (75 mL), brine (75 mL), dry over sodium sulfate, and concentrate under reduced pressure to give a residue. The residue is purified by flash chromatography, eluting with 10-60% ethyl acetate:hexanes to give the title compound (5.3 g, 9.01 mmol, 74%). MS (m/z): 610/612 (M+1).

Provenance & Evidence