Sodium borohydride → HCID 58920620, compound

Participants

Reaction Steps

NaBH4 (600 μg, 0.015 mmol) was added to a solution of N-((S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-3-oxocyclopentanecarboxamide (prepared as described in Example 7, Procedure 12) (7.7 mg, 0.015 mmol) in THF (1 mL) at room temperature. The reaction was monitored by HPLC and after 16 h, the solution was diluted with H2O and extracted with EtOAc (3×). The combined EtOAc layers was further washed with 6N HCl and sat'd aqueous NaCl, dried over Na2SO4, filtered, and concentrated under reduced pressure. Flash chromatography (SiO2, 0-100% EtOAc/hexanes) gave 5.4 mg of N-((S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-3-hydroxycyclopentanecarboxamide as a film. 1H NMR (500 MHz, CDCl3, mixture of isomers) δ 8.54 (s, 1H), 8.52 (s, 1H), 8.35-8.29 (m, 2H), 7.72-7.66 (m, 2H), 7.47-7.42 (m, 2H), 7.40-7.32 (m, 2H), 7.25-7.06 (m, 10H), 6.56-6.50 (m, 4H), 4.48-4.38 (m, 2H), 4.30-4.22 (m, 2H), 3.64-3.53 (m, 2H), 2.89-2.80 (m, 2H), 2.10-0.80 (m, 12H); LC/MS (MeOH/H2O/NH4OAc mobile phase) rt=3.91 min; [M+H]=507.3.

Provenance & Evidence