Triethylamine → HCID 18342549, compound

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Reaction Steps

The title compound was prepared using 2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-cyclohexaneacetic acid, benzyl ester using (75 mg, 0.185 mmol; prepared above as Aldehyde 4), 4-(N-allyl-N-(pyrimid-2-yl)amino)piperidine hydrochloride (61 mg, 0.24 mmol) from Example 2, Step A, NaHB(OAc)3, (97 mg, 0.46 mmol) and triethylamine (0.026 ml, 0.24 mmol) in 3 ml dichloromethane. The mixture was stirred overnight at room temperature. The reaction was diluted with 100 ml EtOAc and washed with 1M NaOH and saturated NaCl. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The material was purified using flash chromatography (5% EtOAc in hexane) to provide 80 mg (71%) of the title compound. HPLC (Zorbax SB-C8 column, 4.6 mm×7.5 cm, Gradient: 90 H2O:10 CH3CN to 0 H2O:100 CH3CN over 7.5 minutes then hold at 100 CH3CN:0 H2O for 45 seconds, 2.25 mL/min, 220 nm): Retention Time: 4.4 minutes.

Provenance & Evidence