(S)-morpholine-3-carboxylic acid → (R)-2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

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Reaction Steps

An enantiomeric mixture of 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 8 g) was dissolved in MeOH (400 mL) and was separated by supercritical fluid chromatography (SFC) (Chiralcel® AS-H (5 μm, 20×150 mm), 20% MeOH in liquid CO2 at 55 mL/min, 3 mL/injection). The peak eluting at ˜5 minutes was collected. The stereo-configuration was assigned based on a comparison of retention times of an enantiomerically-enriched sample synthesized in a manner similar to PREPARATION x1 and PREPARATION x2 using optically pure (S)-morpholine-3-carboxylic acid.

Provenance & Evidence