Dimethylethylamine → benzyl (4aR,7aS)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

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Reaction Steps

Racemic benzyl 2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (30 g, 63 mmol) is chirally purified by SFC: (Column: Chiralpak IC 2.1×25 cm; eluent: 40% methanol/acetonitrile (8/2) with 0.2% dimethylethyl amine in CO2; flow: 70 mL/min at UV 284 nm). The second eluting isomer is the title compound (11.1 g, 37%, >98% ee). Chiral analysis of the isolated isomer 2: Chiralpak IC 0.46×10 cm, 5 μm; eluent: 40% methanol/acetonitrile (8/2) with 0.2% dimethyl ethyl amine in CO2; flow: 5 mL/min at UV 215 nm. Rt=3.2 minutes. [α]D20=−88 (C=1.0, methanol), ES/MS (m/e) 372 (M+H)

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