Methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride → Methyl (2S,4R)-1-{[(3-Chloro-4-cyano-2-methylphenyl)amino]-carbonyl}-4-hydroxypyrrolidine-2-carboxylate

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Reaction Steps

The title compound was prepared from compound 56A (300 mg, 1.65 mmol) and isocyanate 23E (312 mg, 1.62 mmol) by procedures analogous to that described for Example 55A to afford a white foam (375.6 mg, 69%). HPLC: 1.68 min (retention time) (Conditions: YMC S-5 C-18 (4.6×250 mm), eluting with 0-100% B, 4 min gradient. (A=90% H2O-10% CH3CN-0.1% TFA and B=10% H2O-90% CH3CN-0.1% TFA); Flow rate at 4 mL/min. UV detection at 220 nm. Chiral HPLC: retention time=12.92 min (98.9%); Conditions: AD (4.6×250 mm); Eluted with 20% isopropanol in heptane for 30 min at 1 ml/min. MS (ES) m/z 338 [M+H]+.

Provenance & Evidence