Triethylamine → HCID 86758718, compound

Participants

Reaction Steps

The title compound was prepared from 2-(R)-(3-(S)-formyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-cyclohexaneacetic acid, benzyl ester 83 mg, 0.195 mmol; prepared above as Aldehyde 6), 4-(N-allyl-N-(pyrimid-2-yl)-amino)piperidine dihydrochloride (64 mg, 0.219mmol, from Step A), 104 mg (0.49 mmol) NaHB(OAc)3, and 0.035 ml (0.25 mmol) triethylamine 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 83 mg of the title compound. RF: 0.3 (5% EtOAc/hexane). 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: 4.6 minutes.

Provenance & Evidence