Carbon dioxide methanol → (1R,5S)-benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

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Reaction Steps

A racemic mixture of benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (12 g) was resolved under the following conditions: Column: Chiralpak AD-H (5×25 cm, 5 μm), BPR pressure: 100 bars; temperature: 40° C.; flow rate: 290 mL/min; mobile Phase: CO2/MeOH (90/10); Detector Wavelength: 215 nm; injection: 0.83 mL with cycle time 2.6 min; sample preparation: 12.0 g/400 mL MeOH, 30.0 mg/mL. The desired (1R,5S)-benzyl 1-methyl-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate was obtained as the slower eluting peak (4.5 g).

Provenance & Evidence