HCID 66847793, compound → HCID 50903136, compound

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Reaction Steps

The mixture of racemic (4aSR,7aSR)-7a-(4-fluoro-3-(pyrimidin-5-yl)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine and racemic (4aSR,7aSR)-7a-(2-fluoro-5-(pyrimidin-5-yl)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (0.231 g, 0.697 mmol) are separated using a Chiralpak AD-H 3×25 cm column eluting with 3/2 EtOH:acetonitrile with 0.2% dimethylethylamine at a flow rate of 30 mL/min., 225 nM to give (4aS,7aS)-7a-(4-fluoro-3-(pyrimidin-5-yl)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (TR=3.12) (0.032 g, 14%): ES/MS m/e: 331 (M+1) and (4aS,7aS)-7a-(2-fluoro-5-(pyrimidin-5-yl)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-amine (TR=4.479) (0.058 g, 25%). ES/MS m/e: 331 (M+1).

Provenance & Evidence